2-丙烯基-3-丁烯酸酯 | 5453-44-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-丙烯基-3-丁烯酸酯
• 英文名称: allyl crotonate
• 英文别名: prop-2-enyl (E)-but-2-enoate
• CAS: 5453-44-1
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: WNJBUWVXSNLWEQ-HWKANZROSA-N

物化性质

• 沸点：
  174.28°C (rough estimate)
• 密度：
  0.9440

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

毒理性

• 副作用

催泪剂（Lacrimator或Lachrymator）- 一种刺激眼睛并引起流泪的物质。

Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  巴豆酸酐	crotonic anhydride	623-68-7	C8H10O3	154.166
  乙酸烯丙酯	Allyl acetate	591-87-7	C5H8O2	100.117

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2(5H)-呋喃酮	2(5H)-Furanone	497-23-4	C4H4O2	84.0746

反应信息

• 作为反应物：
  描述：

  2-丙烯基-3-丁烯酸酯 在 sodium hydrogen telluride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到巴豆酸
  参考文献：
  名称：

  Shobana, N.; Shanmugam, P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 658

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸烯丙酯 在 samarium diiodide 、 氯甲酸甲酯 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到2-丙烯基-3-丁烯酸酯
  参考文献：
  名称：

  One-Pot Formation of Carbonates from the Reactions of Carbonyl Compounds with Samarium Diiodide and Methyl Chloroformate

  摘要：

  AbstractTreatment of carbonyl compounds with SmI2 and methyl chloroformate in the presence of molecular sieves provides the cyclic carbonates or biscarbonates of pinacols. This one‐pot reaction proceeds rapidly even with aliphatic ketones. The stereochemistry obtained by this procedure is different from that of conventional pinacolic couplings.

  DOI：

  10.1002/jccs.199700043

文献信息

• [EN] SUBSTITUTED BENZYLAMINE COMPOUNDS, THEIR USE IN MEDICINE, AND IN PARTICULAR THE TREATMENT OF HEPATITIS C VIRUS (HCV) INFECTION<br/>[FR] COMPOSÉS DE BENZYLAMINE SUBSTITUÉS, LEUR UTILISATION EN MÉDECINE, EN PARTICULIER DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE C (VHC)
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2013064538A1

  公开（公告）日：2013-05-10

  The invention provides compounds of the formula (I): or a salt, N-oxide or tautomer thereof, wherein A is CH, CF or nitrogen; E is CH, CF or nitrogen; and R0 is hydrogen or C1-2 alkyl; R1a is selected from CONH2; CO2H; an optionally substituted acyclic C1-8 hydrocarbon group; and an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1, 2, 3 or 4 are heteroatom ring members selected from O, N and S; R2 is selected from hydrogen and a group R2a; R2a is selected from an optionally substituted acyclic d-8 hydrocarbon group; an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1 or 2 ring members are heteroatom ring members selected from O, N and S; and an optionally substituted bicyclic heterocyclic group of 9 or 10 ring members, of which 1 or 2 ring members are nitrogen atoms; wherein at least one of R1 and R2 is other than hydrogen; R3 is an optionally substituted 3- to 10-membered monocyclic or bicyclic carbocyclic or heterocyclic ring containing 0, 1, 2 or 3 heteroatom ring members selected from N, O and S; R4a is selected from halogen; cyano; C1-4 alkyl optionally substituted with one or more fluorine atoms; C1-4 alkoxy optionally substituted with one or more fluorine atoms; hydroxy-C1-4 alkyl; and C1-2 alkoxy-C1-4 alkyl; R5 is selected from hydrogen and a substituent R5a; and R5a is selected from C1-2 alkyl optionally substituted with one or more fluorine atoms; C1-3 alkoxy optionally substituted with one or more fluorine atoms; halogen; cyclopropyl; cyano; and amino, The compounds have activity against hepatitis C virus and can be used in the prevention or treatment of hepatitis C viral infections.

  该发明提供了以下式（I）的化合物，或其盐、N-氧化物或互变异构体，其中A为CH、CF或氮；E为CH、CF或氮；R0为氢或C1-2烷基；R1a选自CONH2；CO2H；一个可选择取代的非环状C1-8碳氢化合物基团；以及一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1、2、3或4个是从O、N和S中选择的杂原子环成员；R2选自氢和一个基团R2a；R2a选自一个可选择取代的非环状d-8碳氢化合物基团；一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1或2个环成员是从O、N和S中选择的杂原子环成员；以及一个可选择取代的含有9或10个环成员的双环杂环基团，其中1或2个环成员是氮原子；其中R1和R2中至少一个不是氢；R3选自一个可选择取代的含有0、1、2或3个从N、O和S中选择的杂原子环成员的3至10个成员的单环或双环碳环或杂环环；R4a选自卤素；氰基；C1-4烷基，可选择取代一个或多个氟原子；C1-4烷氧基，可选择取代一个或多个氟原子；羟基-C1-4烷基；和C1-2烷氧基-C1-4烷基；R5选自氢和一个取代基R5a；R5a选自C1-2烷基，可选择取代一个或多个氟原子；C1-3烷氧基，可选择取代一个或多个氟原子；卤素；环丙基；氰基；和氨基。这些化合物对丙型肝炎病毒具有活性，并可用于预防或治疗丙型肝炎病毒感染。
• Cobalt(II)chloride catalysed cleavage of ethers with acyl halides: Scope and mechanism
  作者：Javed Iqbal、Rajiv Ranjan Srivastava

  DOI：10.1016/s0040-4020(01)96041-7

  日期：1991.5

  Cobalt (II) chloride in acetonitrile catalyses the cleavage of a wide variety of ethers with acyl halides under mild conditions to give the corresponding esters in good yields. Acyclic aliphatic ethers are cleaved to the corresponding ester and chlorides whereas the cyclic aliphatic ethers give rise to the ω-chloroesters. The benzyl ethers can be converted to the corresponding esters along with the

  乙腈中的氯化钴（II）在温和的条件下催化多种醚与酰基卤的裂解，从而以高收率得到相应的酯。无环脂族醚裂解成相应的酯和氯化物，而环脂族醚产生ω-氯代酯。苄基醚可与苄基氯和苄基乙酰胺一起形成相应的酯。烯丙基和苄基醚裂解的比较研究表明，苄基醚可以在烯丙基醚存在下选择性裂解。可以以高度区域选择性的方式将环氧乙烷酮裂解为相应的β-氯代酯。乙烯基醚经历sp 2在这些条件下的-杂化的碳-氧键裂解。基于产物分析，讨论了涉及电子转移，随后进行O-酰化以及氯离子对S N 1或S N 2的攻击的机理。
• Selective ene-yne coupling-functionalization: A new strategy in constructing heterocycles
  作者：Zhong Wang、Xiyan Lu

  DOI：10.1016/0040-4020(95)00035-7

  日期：1995.2

  Fluorinated derivatives of 3-alkylidene-2(3H)-dihydrofuranone have been synthesized by sodium dithionite initiated tandem perfluoroalkylation-cyclization of allylic 2-alkynoates in fair to good yield and high stereoselectivity. Fluorinated 3-alkylidene-2(3H)-pyrrolidone derivatives were prepared similarly. A mechanistic rationale concerning the different radical steps and the differences between esters

  通过连二亚硫酸钠引发的烯丙基2-链烷酸酯的串联全氟烷基化-环化反应合成了3-亚烷基-2（3H）-二氢呋喃酮的氟化衍生物，其收率相当好且具有高立体选择性。类似地制备氟化的3-亚烷基-2（3H）-吡咯烷酮衍生物。给出了关于不同的自由基步骤以及酯和酰胺之间的差异的机械原理。
• [EN] COMPOSITION FOR TIN-SILVER ALLOY ELECTROPLATING COMPRISING A COMPLEXING AGENT<br/>[FR] COMPOSITION POUR L'ÉLECTROGALVANISATION D'ALLIAGE D'ÉTAIN ET D'ARGENT COMPRENANT UN AGENT COMPLEXANT
  申请人：BASF SE

  公开号：WO2019185468A1

  公开（公告）日：2019-10-03

  An aqueous composition comprising (a) metal ions comprising tin ions and silver ions and (b) at least one complexing agent of formula (C1) R1-X1-S-X21[D1-X22-]nS-X3-R2, (C2) R1-X1-S-X31-D2-[X32-S-]nX3-R2, (C3) R3-X1-S-X41-[D3-X42-]nS-X3-R4 wherein X1, X3 are independently selected from a linear or branched C1-C12 alkanediyl, which may be unsubstituted or substituted by OH; X21, X22 are independently selected from X1, which may be further substituted by -X5-COOR12, -X5-SO2-O-R12, a C2 to C6 polyoxyalkylene group of formula -(O-CH2- CHR11)z-OH, or a combination thereof, and -X1-NH-CO-X6-CO-NH-X1-; X31, X32 are independently selected from a chemical bond and X1; X41, X42 are independently selected from X1; X5 is a linear or branched Ci to C10 alkyl; X6 is selected from X1 and a divalent 5 or 6 membered aromatic group; R1, R2 are independently selected from a monovalent 5 or 6 membered aromatic N- heterocyclic group comprising one N atom or two N atoms which are separated by at least one C atom, and its derivatives received by N-alkylation with a C1-C6- alkyl group, which may be substituted by --COOR12 or -SO2-O-R12, and which aromatic N- heterocyclic group may optionally further comprise, under the proviso that X21 is substituted by at least one OH, one S atom; R3, R4 are independently selected from a monovalent 5 or 6 membered aliphatic N- heterocyclic group comprising one N atom and one O atom; D1 is independently selected from S, O and NR10-; D2 is (a) a divalent 5 or 6 membered aliphatic heterocyclic ring system comprising 1 or 2 S atoms, or (b) a 5 or 6 membered aromatic heterocyclic ring system comprising at least two N atoms and optionally one or two S atoms; D3 is independently selected from S and NR10-; n is an integer of from 0 to 5; z is an integer from 1 to 50; R10 is selected from H and a linear or branched C1-C12 alkyl; R11 is selected from H and a linear or branched C1 to C6 alkyl; and R12 is selected from R10 and a cation.

  一种水性组合物，包括（a）包括锡离子和银离子的金属离子和（b）至少一种具有以下结构的络合剂：（C1）R1-X1-S-X21[D1-X22-]nS-X3-R2，（C2）R1-X1-S-X31-D2-[X32-S-]nX3-R2，（C3）R3-X1-S-X41-[D3-X42-]nS-X3-R4，其中X1、X3可独立地选择自线性或支链的C1-C12脂肪二亚基，可以未取代或被OH取代；X21、X22可独立地选择自X1，可以进一步被-X5-COOR12，-X5-SO2-O-R12，具有式-(O-CH2-CHR11)z-OH的C2到C6聚氧烷基，或其组合物取代，以及-X1-NH-CO-X6-CO-NH-X1-；X31、X32可独立地选择自化学键和X1；X41、X42可独立地选择自X1；X5是线性或支链的Ci到C10烷基；X6选择自X1和双价的5或6元芳香族基；R1、R2可独立地选择自包括一个N原子或两个N原子的单价5或6元芳香N-杂环基，通过N-烷基化与C1-C6烷基基团取代的衍生物，可以被--COOR12或-SO2-O-R12取代，该芳香N-杂环基可以选择性地进一步包括，在X21至少被一个OH取代的条件下，一个S原子；R3、R4可独立地选择自包括一个N原子和一个O原子的单价5或6元脂肪N-杂环基；D1可独立地选择自S、O和NR10-；D2是（a）包括1或2个S原子的双价5或6元脂肪杂环环系统，或（b）包括至少两个N原子和可选地一个或两个S原子的5或6元芳香杂环环系统；D3可独立地选择自S和NR10-；n是从0到5的整数；z是从1到50的整数；R10选择自H和线性或支链的C1-C12烷基；R11选择自H和线性或支链的C1到C6烷基；R12选择自R10和阳离子。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。

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