顺式-4-癸烯酸 | 505-90-8

• 物质功能分类: 食品添加剂 - 食品香料 - 人造香料
• 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: 顺式-4-癸烯酸
• 中文别名: 顺-4-癸烯酸
• 英文名称: (Z)-dec-4-enoic acid
• 英文别名: cis-dec-4-enoic acid；(Z)-4-Decenoic acid；cis-4-decenoic acid；Z-4-decenoic acid；dec-4c-enoic acid
• CAS: 505-90-8
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: XKZKQTCECFWKBN-SREVYHEPSA-N

物化性质

• 熔点：
  18.83°C (estimate)
• 沸点：
  290.67°C (estimate)
• 密度：
  0.9366 (rough estimate)
• LogP：
  3.531 (est)
• 物理描述：
  Liquid
• 溶解度：
  soluble in oil
• 折光率：
  0.915-0.925

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  顺式-4-癸烯酸 在 palladium diacetate 氧气 、 sodium acetate 作用下， 以 二甲基亚砜 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 72.0h， 以81%的产率得到5-[(1E)-1-hexenyl]dihydro-2(3H)-furanone
  参考文献：
  名称：

  Synthesis of unsaturated lactones via palladium-catalyzed cyclization of alkenoic acids

  摘要：

  Acyclic and cyclic, aliphatic or aromatic, 4- or 5-alkenoic acids cyclize in high yield to 5- or 6-membered unsaturated lactones using 5 mol % Pd (OAc) 2, 2 equiv of NaOAc, and 1 atm Of O2.

  DOI：

  10.1021/jo00072a004
• 作为产物：
  描述：

  在 sodium hydroxide 、 水 作用下， 以 二甲基亚砜 为溶剂， 生成 顺式-4-癸烯酸
  参考文献：
  名称：

  IBX-Mediated Oxidation of Primary Alcohols and Aldehydes To Form Carboxylic Acids

  摘要：

  DOI：

  10.1002/1521-3773(20021104)41:21<4059::aid-anie4059>3.0.co;2-r

文献信息

• [EN] LYMPHATIC SYSTEM-DIRECTING LIPID PRODRUGS<br/>[FR] PROMÉDICAMENTS LIPIDIQUES ORIENTANT VERS LE SYSTÈME LYMPHATIQUE
  申请人：ARIYA THERAPEUTICS INC

  公开号：WO2019046491A1

  公开（公告）日：2019-03-07

  The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a provided lipid prodrug or a pharmaceutical composition thereof.

  本发明提供了淋巴系统定向脂质前药，其制药组合物，制备这种前药和组合物的方法，以及改善作为脂质前药一部分的治疗剂的生物利用度或其他性质的方法。本发明还提供了治疗疾病、紊乱或症状的方法，包括向需要的患者施用所提供的脂质前药或其制药组合物。
• METHOD FOR THE SYNTHESIS OF DIACIDS OR DIESTERS FROM NATURAL FATTY ACIDS AND/OR ESTERS
  申请人：Dubois Jean-Luc

  公开号：US20100305354A1

  公开（公告）日：2010-12-02

  The invention relates to a process for the synthesis of diacids or diesters of general formula ROOC—(CH 2 ) x —COOR, in which n is an integer between 5 and 14, R is either H or an alkyl radical of 1 to 4 carbon atoms, from natural long-chain monounsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule of the general formula CH 3 —(CH 2 ) n —CHR 1 —CH 2 —CH═CH—(CH 2 ) p —COOR, in which R is H or an alkyl radical with 1 to 4 carbon atoms, R 1 is either H or OH, and n and p, which are equal or different and are indices between 2 and 11. The method comprises: during a first step, converting the natural fatty acid or ester by pyrolysis or by ethenolysis, into a ω-monounsaturated fatty acid or ester of the general formula CH 2 ═CH—(CH 2 ) m —COOR, in which m is equal to p or p+1, depending on the nature of the processed fatty acid/ester and the conversion used; during a second step, submitting the product thus obtained to a metathesis or homometathesis reaction for obtaining a compound of the general formula ROOC—(CH 2 ) m —CH═CH—(CH 2 ) m —COOR, or cross-metathesis with a compound of formula R 2 OOC—(CH 2 ) r —CH═CH—R 3 , in which R 2 is either H or an alkyl radical front with 1 to 4 carbon atoms, r is either 0 or 1 or 2 and R 3 is H, CH 3 or COOR 2 , thus defining a cyclic or molecule or not, in order to obtain an unsaturated compound of the general formula ROOC—(CH 2 ) m —CH═CH—(CH 2 ) r —COOR 2 , and during a third step, converting the unsaturated compound into a saturated compound by hydrogenation of the double bond.

  这项发明涉及一种合成一般公式为ROOC—(CH2)x—COOR的二元酸或二元酯的过程，其中n是5到14之间的整数，R是H或1到4个碳原子的烷基自由基，从天然长链单不饱和脂肪酸或酯中合成，这些脂肪酸或酯每分子至少包括10个相邻的碳原子，其一般公式为CH3—(CH2)n—CHR1—CH2—CH═CH—(CH2)p—COOR，其中R是H或1到4个碳原子的烷基自由基，R1是H或OH，n和p相等或不同，是2到11之间的指数。该方法包括：在第一步中，通过热解或乙炔醇解将天然脂肪酸或酯转化为ω-单不饱和脂肪酸或酯，其一般公式为CH2═CH—(CH2)m—COOR，其中m等于p或p+1，具体取决于处理的脂肪酸/酯的性质和所使用的转化；在第二步中，将所得产物进行交叉代谢或同交叉代谢反应，以获得一般公式为ROOC—(CH2)m—CH═CH—(CH2)m—COOR的化合物，或与公式为R2OOC—(CH2)r—CH═CH—R3的化合物进行交叉代谢，其中R2是H或1到4个碳原子的烷基自由基，r是0或1或2，R3是H、CH3或COOR2，从而定义一个循环或不循环的分子，以获得一般公式为ROOC—(CH2)m—CH═CH—(CH2)r—COOR2的不饱和化合物；在第三步中，通过加氢双键将不饱和化合物转化为饱和化合物。
• Enantioselective Epoxidation of Nonconjugated <i>cis</i>-Olefins by Chiral Dioxirane
  作者：Christopher P. Burke、Yian Shi

  DOI：10.1021/ol901724v

  日期：2009.11.19

  A variety of nonconjugated cis-olefins has been enantioselectively epoxidized with chiral ketones 2, and up to 92% ee has been obtained. The two prochiral faces of an olefin are likely stereodifferentiated by the relative hydrophobicity of the olefin substituents and/or allylic oxygen functionality.

  多种非共轭顺式烯烃已与手性酮2对映选择性环氧化，获得了高达 92% 的 ee。烯烃的两个前手性面可能因烯烃取代基和/或烯丙基氧官能团的相对疏水性而立体分化。
• [EN] LIPID PRODRUGS OF PREGNANE NEUROSTEROIDS AND USES THEREOF<br/>[FR] PROMÉDICAMENTS LIPIDIQUES DE NEUROSTÉROÏDES DE PRÉGNANE ET LEURS UTILISATIONS
  申请人：PURETECH HEALTH LLC

  公开号：WO2020028787A1

  公开（公告）日：2020-02-06

  The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.

  本发明提供了淋巴系统定向脂质前药，以及其制药组合物、生产这种前药和组合物的方法，以及改善作为脂质前药一部分的治疗剂的生物利用度或其他性质的方法。本发明还提供了治疗疾病、紊乱或症状的方法，包括向需要的患者施用所述的脂质前药或其制药组合物。
• METHOD FOR SYNTHESIZING AN OMEGA-AMINO ACID OR ESTER FROM A MONOUNSATURATED FATTY ACID OR ESTER
  申请人：Couturier Jean-Luc

  公开号：US20140187808A1

  公开（公告）日：2014-07-03

  A method for synthesizing ω-amino-alkanoic acids or the esters thereof from natural unsaturated fatty acids passing through an intermediate ω-unsaturated nitrile compound. The method is simple to implement and, relative to known methods, avoids the environmental constraints and economic disadvantages resulting from the reaction by-products. The method includes synthesizing an ω-amino acid (ester) of formula R3OOC—(CH2) q —CH2NH2, in which R3 is H or an n-butyl radical and q is an integral index of between 2 and 13, from a monounsaturated fatty acid (ester) of formula (R1-CH═CH—(CH2)p-COO) xR2, in which x represents 1, 2 or 3, R1 is H or a hydrocarbon radical comprising from 4 to 11 carbon atoms and, where appropriate, a hydroxyl function, R2 is H or an alkyl radical comprising from 2 to 4 carbon atoms, and may contain one or more heteroatoms, and p is an integral index of between 2 and 11, including a reaction step of ammoniation.

  一种从天然不饱和脂肪酸通过中间体ω-不饱和腈化合物合成ω-氨基-烷酸或其酯的方法。该方法实施简单，与已知方法相比，避免了由反应副产物导致的环境限制和经济劣势。该方法包括从公式为(R1-CH═CH—(CH2)p-COO)xR2的单不饱和脂肪酸(酯)合成公式为R3OOC—(CH2)q—CH2NH2的ω-氨基酸(酯)，其中R3是H或n-丁基基团，q是2到13之间的整数指数，x代表1、2或3，R1是H或含4到11个碳原子的烃基团，适当情况下还含有羟基，R2是H或含2到4个碳原子的烷基基团，可包含一个或多个杂原子，p是2到11之间的整数指数，包括氨化反应步骤。