2,2-dimethylpropyl cinnamate | 138964-29-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2,2-dimethylpropyl cinnamate
• 英文别名: neopentyl (E)-cinnamate；2,2-dimethylpropyl (E)-3-phenylprop-2-enoate
• CAS: 138964-29-1
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: AJJQXLYDATVLHW-MDZDMXLPSA-N

物化性质

• 沸点：
  307.5±11.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  neopentyl (2R*,3R*)-2-(tert-butyldimethylsilyl)-3-hydroxy-3-phenylpropionate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到2,2-dimethylpropyl cinnamate
  参考文献：
  名称：

  Chemistry of silylketenes: a simple preparation of α-silyl-α-stannylacetic esters and their stereoselective Reformatsky-type reaction with aldehydes or aldimines

  摘要：

  Silylketenes 1a, b reacted smoothly with alkoxystannanes 3 to give the corresponding alpha-silyl-alpha-stannylacetates 4 almost quantitatively. Treatment of 4 with TiCl4 caused selective cleavage of the C-Sn bond to bring about Reformatsky-type reaction with aldehydes 6 giving beta-hydroxy-alpha-silyl esters 7. These two steps were carried out by one-pot operation, and variously substituted compounds 7 were obtained with high syn-selectivity (52-> 96% d.e.) in 41-89% yields. A similar one-pot procedure starting from la-c, 3, and aldimines 11 also provided the corresponding beta-amino-alpha-silyl esters 12 with excellent syn-selectivity (greater-than-or-equal-to 96% d.e.) in 64-94% yields. Stereocontrolled preparation of both (E)- and (Z)-alpha,beta-unsaturated esters 8 and a syn-amino diol derivative 17 from syn-7 and syn-12, respectively, is also described.

  DOI：

  10.1039/p19920002813

文献信息

• Borrowing Hydrogen: Indirect “Wittig” Olefination for the Formation of C–C Bonds from Alcohols
  作者：Phillip J. Black、Michael G. Edwards、Jonathan M. J. Williams

  DOI：10.1002/ejoc.200600070

  日期：2006.10

  development of an indirect three-step domino sequence for the formation of C-C bonds from alcohol substrates is described. An iridium-catalysed dehydrogenation of alcohol I affords the intermediate aldehyde 2. The desired C-C bond can then be formed by a facile Wittig olefination, yielding the intermediate alkene 3. In the final step the alkene is hydrogenated to afford the indirect Wittig product, the

  描述了从醇底物形成 CC 键的间接三步多米诺骨牌序列的成功开发。醇 I 的铱催化脱氢得到中间体醛 2。然后可以通过简单的 Wittig 烯化形成所需的 CC 键，产生中间体烯烃 3。在最后一步中，烯烃被氢化以提供间接的 Wittig 产物，即烷烃 4. 这个过程的关键是借氢的概念；在最初的脱氢步骤中除去的氢气被铱催化剂简单地借用。作为储氢器，催化剂促进 CC 键的形成，然后在最后一步返回借用的氢。在此，我们将详细介绍我们对底物和反应范围以及催化循环的局限性的研究。((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)。
• Catalytic Electronic Activation: Indirect “Wittig” Reaction of Alcohols
  作者：Michael G. Edwards、Jonathan M. J. Williams

  DOI：10.1002/anie.200290034

  日期：2002.12.16
• Gelebe, Aifheli C.; Kaye, Perry T., South African Journal of Chemistry, 1994, vol. 47, # 1, p. 26 - 28
  作者：Gelebe, Aifheli C.、Kaye, Perry T.

  DOI：——

  日期：——
• Getebe Aifheli C., Kaye Perry T., S. Afr. J. Chem, 47 (1994) N 1, S 26-28
  作者：Getebe Aifheli C., Kaye Perry T.

  DOI：——

  日期：——