methyl (Z)-2-undecenoate | 54299-03-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-2-undecenoate
• 英文别名: cis-Undec-2-ensaeure-methylester；Methyl cis-undecenoate；methyl (Z)-undec-2-enoate
• CAS: 54299-03-5
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: FDNCPIRKQFHDBX-KHPPLWFESA-N

物化性质

• 沸点：
  254.9±9.0 °C(Predicted)
• 密度：
  0.886±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-癸炔 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 methyl (Z)-2-undecenoate
  参考文献：
  名称：

  蜂王浆的成分：10-羟基-反式-癸-2-烯酸

  摘要：

  引用了化学和物理证据，其证明从蜂王浆中分离的10-羟基癸-2-烯酸中的烯键具有反式构型。

  DOI：

  10.1016/0040-4020(62)80037-4

文献信息

• ortho-Metalated dirhodium(II)-catalyzed α-diazocarbonyl transformation. Diastereoselective cyclopropanation of menthyl-α-diazo-β-keto ester and CH insertion of α-diazo ester
  作者：Pascual Lahuerta*、Inés Pereira、Julia Pérez-Prieto*、Mercedes Sanaú、Salah-Eddine Stiriba*、Douglass F Taber*

  DOI：10.1016/s0022-328x(00)00357-0

  日期：2000.10

  obtaining 71 and 85%, respectively, of the 1,5-CH insertion product, trans-2-pentylcyclopentanecarboxylate (8) versus 1,2-elimination product, (Z)-2-undecenoate (9) (29 and 15%, respectively). The three possible diastereomers of catalyst (1d) which possess two ortho-metalated P(C6H5)2(C6F5) ligands in a head-to-tail configuration, with the two pentafluorophenyl groups in an endo–endo, endo–exo or exo–exo

  包含两种金属化的P（C 6 H 5）2（C 6 F 5）和两种乙酸盐的邻位金属铑（II）化合物（1d 1）已成功催化了薄荷基-2-重氮-3-氧代-6-庚酸酯的环丙烷化反应（4）形成具有显着的顺-反（30:70）非对映选择性的环丙烷6和7。2d 1和2d 4介导了2-二氮杂癸酸甲酯（5）环化的增强性能催化剂，分别获得71％和85％的1,5-CH插入产物反-2-戊基环戊烷羧酸酯（8）与1,2-消除产物（Z）-2-十一碳烯酸酯（9）（29）和15％）。催化剂（1d）的三种可能的非对映异构体，具有首尾相接的两个邻位金属化P（C 6 H 5）2（C 6 F 5）配体，并且在一个内-内结构中具有两个五氟苯基，内部– exo或exo –exo配置已通过标准柱色谱分离。对其中两个异构体1d 3 endo - exo和1d 1 end - endo的X射线结构分析，可以对其结构进行分配。
• Stereocontrolled synthesis of α,β-unsaturated carboxylic esters from O-methyl-C,O-bis(trimethylsilyl)ketene acetal and aliphatic aldehydes
  作者：Isamu Matsuda、Yusuke lzumi

  DOI：10.1016/s0040-4039(01)90445-9

  日期：1981.1

  (R*,S*) Selective aldol type reaction of O-methyl-C,O-bis(trimethylsilyl)ketene acetal () with aldehydes and stereoselective formation of α,β-unsaturated carboxylic esters are attained by the combination of Z- and Lewis acids.

  （R *，S *）O-甲基-C，O-双（三甲基甲硅烷基）乙烯酮缩醛（）与醛的选择性羟醛型反应，通过Z-和C-的结合可实现立体选择性地形成α，β-不饱和羧酸酯路易斯酸。
• A Convenient Method for the Preparation of (<i>Z</i>)-α,β-Unsaturated Carbonyl Compounds
  作者：Douglass F. Taber、R. Jason Herr、Shawn K. Pack、John M. Geremia

  DOI：10.1021/jo952098j

  日期：1996.1.1
• Rhodium-Mediated Intramolecular C−H Insertion:  Probing the Geometry of the Transition State
  作者：Douglass F. Taber、Scott C. Malcolm

  DOI：10.1021/jo9803434

  日期：1998.5.1

  The unsymmetrical alpha-diazo ester 1b, derived from the chiral naphthylborneol 5, was cyclized with a set of rhodium carboxylates (L = CF3CO2, CH3CO2, CH3(CH2)(6)CO2, (CH3)(3)CCO2). The ratio of the three major products ((R,R)-3b, (S,S)-3b, 4b) was determined. It was found that the rhodium catalyst derived from pivalic acid gave the highest ratio of 3b:4b. Lowering the temperature of the reaction (L = (CH3)(3)CCO2) increased both the yield and the diastereoselectivity of the cyclization. From these results and from our computational analysis, it is concluded that the ester carbonyl and the rhodium carbenoid are probably syn in the transition state leading to cyclization.
• LAROCK, R. C.;NARAYANAN, KRISHNASWAMY, J. ORG. CHEM., 1984, 49, N 18, 3411-3413
  作者：LAROCK, R. C.、NARAYANAN, KRISHNASWAMY

  DOI：——

  日期：——