methyl 3-cyclohexylideneacrylate | 17179-64-5

• 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 3-cyclohexylideneacrylate
• CAS: 17179-64-5
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: PDKXIOQADUKWNC-UHFFFAOYSA-N

物化性质

• 沸点：
  247.3±7.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-cyclohexylideneacrylate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,2-双(二苯基膦)乙烷 作用下， 反应 14.0h， 生成 methyl (E)-3-(1-cyclohexenyl)-2-propenoate
  参考文献：
  名称：

  钯催化的炔丙基碳酸酯的羰基化：2,3-和2,4-二烯基羧酸酯的制备

  摘要：

  DOI：

  10.1016/s0040-4039(00)84086-1
• 作为产物：
  描述：

  methyl (1-(3-oxoprop-1-yn-1-yl)cyclohexyl)carbonate 在 4,5,6,7-四氢-3-(2,4,6-三甲基苯基)-苯并噻唑高氯酸盐 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 32.0h， 以79%的产率得到methyl 3-cyclohexylideneacrylate
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Internal Redox Reaction of Alkynals: An Efficient Synthesis of Allenoates

  摘要：

  An efficient N-heterocyclic carbene (NHC)-catalyzed internal redox reaction of alkynals that bear a y leaving group has been developed. This process provides a new access to a range of allenoates in good yields. Preliminary results demonstrate that the enantioselective variant can also be achieved.

  DOI：

  10.1021/ol300111m

文献信息

• Stereoselective synthesis of (Z )-α-(alkoxycarbonyl)methylene β- and γ-lactones by palladium-catalysed oxidative carbonylation of alkynols
  作者：Bartolo Gabriele、Giuseppe Salerno、Francesca De Pascali、Mirco Costa、Gian Paolo Chiusoli

  DOI：10.1039/a603892a

  日期：——

  (Z)-α-(Alkoxycarbonyl)methylene β- and γ-lactones can be obtained in fair to excellent yields and with high catalytic efficiencies by PdI2/KI-catalysed oxidative dialkoxycarbonylation of propynyl alcohols (α,α-dialkyl substituted, or α-monoalkyl substituted with a sufficiently bulky alkyl group) and but-3-yn-1-ols, respectively. Reactions are carried out in alcoholic media under mild conditions (70–80 °C and 20 atm of a 3∶1 mixture of carbon monoxide and air). Reaction pathways are discussed.

  (Z)-δ-(烷氧基羰基)亚甲基δ-和δ-内酯可分别通过 PdI2/KI 催化的丙炔醇（δ,δ-二烷基取代，或δ-单烷基被足够大的烷基取代）和丁-3-炔-1-醇的氧化二烷氧基羰基化反应，以相当好到极好的产率和较高的催化效率获得。反应在酒精介质中温和进行（70â80 °C，20 atm 的一氧化碳和空气 3â¶1 混合物）。对反应途径进行了讨论。
• Synthesis of tetrasubstituted thiophenes <i>via</i> a [3+2] cascade cyclization reaction of pyridinium 1,4-zwitterionic thiolates and activated allenes
  作者：Shengxian Zhai、Xinping Zhang、Bin Cheng、Hui Li、Yuntong Li、Yixuan He、Yun Li、Taimin Wang、Hongbin Zhai

  DOI：10.1039/d0cc00262c

  日期：——

  A [3+2] cascade cyclization reaction of pyridinium 1,4-zwitterionic thiolates and activated allenes has been developed, which allows facile access to a library of tetrasubstituted thiophenes with great variety under thermal conditions.

  已经开发了吡啶鎓的1，4-两性离子硫醇盐和活化的烯基的[3 + 2]级联环化反应，该反应允许在热条件下容易地访问种类繁多的四取代噻吩文库。
• Copper(II)‐Catalyzed Cascade Reactions of <i>N</i> ‐Aryl Nitrones and Disubstituted Allenoates to Prepare [1,3]Oxazino[3,2‐a]indolines and Dihydropyrido[1,2‐a]indolines
  作者：Pei‐Pei Xu、Su‐Ge Xin、Xue Li、Cui Liang、Dong‐Liang Mo

  DOI：10.1002/adsc.202201403

  日期：2023.3.7

  We described a copper(II)-catalyzed [3+2] cycloaddition of N-aryl-α,β-unsaturated nitrones with disubstituted allenoates bifurcated to prepare various [1,3]oxazino[3,2-a]indolines and dihydropyrido[1,2-a]indolines in moderate to excellent yields. Mechanistic studies revealed that [1,3]oxazino[3,2-a]indoline was a kinetically favored product and dihydropyrido[1,2-a]indoline was thermodynamically favored

  我们描述了铜 (II) 催化的 [3+2] 环加成反应N -芳基-α,β-不饱和硝酮与二取代的联烯酸酯分叉以制备各种 [1,3]恶嗪并 [3,2-a] 二氢吲哚和二氢吡啶并 [ 1,2-a]二氢吲哚的产量适中。机理研究表明，[1,3]恶嗪并[3,2-a] 吲哚啉是一种动力学上有利的产物，而二氢吡啶并[1,2-a] 吲哚啉是一种热力学上有利的产物。此外，该反应易于在克级进行，并且可以通过使用手性助剂获得手性二氢吡啶并[1,2-a]二氢吲哚。本方法突出了广泛的底物范围、良好的官能团耐受性以及具有高非对映选择性的二氢吲哚支架的多样性。
• α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals
  作者：Xu Wang、Zijun Wu、Jian Wang

  DOI：10.1021/acs.orglett.5b03615

  日期：2016.2.5

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.
• TSUJI, JIRO;SUGIURA, TERUO;MINAMI, ICHIRO, TETRAHEDRON LETT., 1986, 27, N 6, 731-734
  作者：TSUJI, JIRO、SUGIURA, TERUO、MINAMI, ICHIRO

  DOI：——

  日期：——