(E)-3-(3-pyridyl)allyl acetate | 132376-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-3-(3-pyridyl)allyl acetate
• 英文别名: 3-(3-pyridyl)allyl acetate；[(E)-3-pyridin-3-ylprop-2-enyl] acetate
• CAS: 132376-76-2
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: VZJUXZJCVLYTHF-HWKANZROSA-N

物化性质

• 沸点：
  304.9±30.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-(naphthalen-1-ylmethyl)indolin-2-one 、 (E)-3-(3-pyridyl)allyl acetate 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 C₃₈H₃₄NO₄P 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 3-hydroxy-1-(naphthalen-1-ylmethyl)-3-(-1-(pyridin-3-yl)allyl)indolin-2-one
  参考文献：
  名称：

  Iridium-Catalyzed Enantioselective and Diastereoselective Allylation of Dioxindoles: A One-Step Synthesis of 3-Allyl-3-hydroxyoxindoles

  摘要：

  An iridium-catalyzed asymmetric allylation of dioxindoles, 3-hydroxyoxindoles, regulated by prosthetic groups has been accomplished under mild conditions. The methodology is applicable to a diverse array of 3-hydroxyoxindole and cinnamyl acetate substrates. A range of 3-ally'-3-hydroxyoxindoles containing vicinal tetrasubstituted and trisubstituted stereocenters can be efficiently synthesized in one-step with excellent enantioselectivity (up to >99% enaniomeric excess (ee)) and good diastereoselectivity (up to 11:1 diastereomeric ratio (dr)).

  DOI：

  10.1021/acs.orglett.8b02655
• 作为产物：
  描述：

  3-吡啶甲醛 在 4-二甲氨基吡啶 、 sodium 、 二异丁基氢化铝 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 29.0h， 生成 (E)-3-(3-pyridyl)allyl acetate
  参考文献：
  名称：

  Construction of polycyclic compounds by cyclocarbonylation. 6. Palladium-catalyzed cyclocarbonylation of 3-(heteroaryl)allyl acetates

  摘要：

  Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130-170-degrees-C under 50-70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively. The synthetic utility of the reaction was demonstrated by the synthesis of cannabifuran from isothymol.

  DOI：

  10.1021/jo00005a046

文献信息

• [EN] SYNTHESIS METHOD AND INTERMEDIATES USEFUL IN THE PREPARATION OF PYRROLOBENZODIAZEPINES<br/>[FR] PROCÉDÉ DE SYNTHÈSE ET INTERMÉDIAIRES POUVANT SERVIR À PRÉPARER DES PYRROLOBENZODIAZÉPINES
  申请人：SPIROGEN SARL

  公开号：WO2013053872A1

  公开（公告）日：2013-04-18

  A compound of formula I wherein: R7 is selected from: ORA, where RA is selected from C1-4 saturated alkyl, optionally substituted by phenyl, which may bear a chloro substituent, pyridyl and furanyl; chloro; NH2; -CH2-O-C(=O)Me; R8 is OProt°, where Prot° is a silicon-based oxygen protecting group orthogonal to Rc; R9 is selected from H, methyl and methoxy; Rs is selected from CF3, (CF2)3CF3, CH3 and (formula 2) and Rc is selected from: (i) -C(=O)-ORC1, where RC1 is a saturated C1-4 alkyl group; (ii) -CH2-O-C(=0)RC2, where RC2 is methyl or phenyl; (iii) -CH2-O-Si-(RSi1)(RSi2)(RSi3), where RSi1, RSi2, RSi3 are independently selected from C1-6 a saturated alkyl group and a phenyl group; and (iv) -C(-YRC3)(-YRC4) where each Y is independently O or S, and where RC3 and RC4 are independently a saturated C1-4 alkyl group, or together form a C2-3 alkylene.

  式I的化合物，其中：R7选自：ORA，其中RA选自C1-4饱和烷基，可选择地被苯基取代，该苯基可能带有氯取代基，吡啶基和呋喃基；氯；NH2；-CH2-O-C(=O)Me；R8为OProt°，其中Prot°是与Rc正交的基于硅的氧保护基团；R9选自H，甲基和甲氧基；Rs选自CF3，(CF2)3 ，CH3和（式2）；Rc选自：(i)-C(=O)-ORC1，其中RC1是饱和的C1-4烷基基团；(ii)- -O-C(=0)RC2，其中RC2是甲基或苯基；(iii)- -O-Si-(RSi1)(RSi2)(RSi3)，其中RSi1，RSi2，RSi3分别选自C1-6饱和烷基和苯基；以及(iv)-C(-YRC3)(-YRC4)，其中每个Y独立地为O或S，且RC3和RC4独立地为饱和的C1-4烷基基团，或者一起形成C2-3亚烷基。
• INTERMEDIATES USEFUL FOR THE SYNTHESIS OF PYRROLOBENZODIAZEPINES
  申请人：Howard Philip Wilson

  公开号：US20130035484A1

  公开（公告）日：2013-02-07

  A compound of formula (I): which is substantially free of any of the corresponding compound of formula (IB): methods of making such compounds, and the further transformation of such compounds.

  具有化学式（I）的化合物：基本上不含有任何具有化学式（IB）的相应化合物；制备这类化合物的方法，以及这类化合物的进一步转化。
• A palladium NNC-pincer complex: an efficient catalyst for allylic arylation at parts per billion levels
  作者：Go Hamasaka、Fumie Sakurai、Yasuhiro Uozumi

  DOI：10.1039/c4cc09726b

  日期：——

  Allylic arylation of allylic acetates by sodium tetraarylborates in the presence of ppb to ppm (molar) loadings of a palladium NNC-pincer complex catalyst in methanol at 50 °C gave the corresponding arylated products in excellent yields.

  在50°C下，甲醇中存在ppb到ppm（摩尔）负载的钯NNC-夹持配合物催化剂的情况下，烯丙基乙酸酯通过钠四芳基硼酸盐的烯丙基芳基化反应以极高产率得到相应的芳基化产物。
• Synthesis and Anti-HIV Activity of Novel N-1 Side Chain-Modified Analogs of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)
  作者：Renée Pontikis、Rachid Benhida、Anne-Marie Aubertin、David S. Grierson、Claude Monneret

  DOI：10.1021/jm960765a

  日期：1997.6.1

  1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (1, HEPT) were synthesized and evaluated for their anti-HIV-1 activity. In particular, the influence of substitution of the terminal hydroxy group of the acyclic structure of HEPT and the structural rigidity of this side chain were investigated. Halo (7, 8), azido (9), and amino (10-15) derivatives were synthesized from HEPT via the p-tosylate derivative 6. Acylation

  合成了一系列33种N-1的1-[（（2-羟基乙氧基）甲基] -6-（苯硫基）胸腺嘧啶（1，HEPT）的N-1侧链修饰的类似物，并评估了它们的抗HIV-1活性。特别地，研究了HEPT的无环结构的末端羟基的取代和该侧链的结构刚性的影响。经由对甲苯磺酸酯衍生物6由HEPT合成卤代（7、8），叠氮基（9）和氨基（10-15）衍生物。伯胺15的酰化提供了酰胺基类似物16-20。通过在三正丁基膦的存在下使HEPT或6-（2-吡啶硫基）类似物23与二芳基二硫化物反应来制备二芳基衍生物26-29。化合物39-41，其中N-1侧链通过掺入E-构型的双键而硬化，
• Synthesis of deoxy analogs of HEPT involving a palladium (0) catalyzed coupling
  作者：Renée Pontikis、Claude Monneret

  DOI：10.1016/s0040-4039(00)73352-1

  日期：1994.6

  Deoxy analogs of HEPT (4-7) were prepared by Pd(0) catalyzed coupling between 6-(phenylthio)thymine and cinnamyl acetate or 3-(heteroaryl) allyl acetates.