3-phenylhexanoic acid methyl ester | 861659-75-8

• 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: 3-phenylhexanoic acid methyl ester
• 英文别名: methyl 3-phenylhexanoate；(S)-methyl 3-phenylhexanoate；(+)(S)-β-Phenyl-capronsaeure-methylester；methyl (3S)-3-phenylhexanoate
• CAS: 861659-75-8
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: BWMQAZHCKKAAGM-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2-溴苯甲醚 、 3-phenylhexanoic acid methyl ester 生成 (+)(S)-1,1-Di-o-anisyl-3-phenyl-hexanol-(1)
  参考文献：
  名称：

  Studies on the 4-Hydroxycoumarins. XVII.^1a The Resolution and Absolute Configuration of Warfarin^1b

  摘要：

  DOI：

  10.1021/ja01473a020
• 作为产物：
  描述：

  重氮甲烷 、 (3S)-3-phenylheptanoic acid 生成 3-phenylhexanoic acid methyl ester
  参考文献：
  名称：

  Studies on the 4-Hydroxycoumarins. XVII.^1a The Resolution and Absolute Configuration of Warfarin^1b

  摘要：

  DOI：

  10.1021/ja01473a020

文献信息

• Rhodium-catalyzed asymmetric 1,4-addition of arylboron reagents to α,β-unsaturated esters
  作者：Yoshiaki Takaya、Taichi Senda、Hiroaki Kurushima、Masamichi Ogasawara、Tamio Hayashi

  DOI：10.1016/s0957-4166(99)00417-6

  日期：1999.10

  Reaction of arylboron reagents, arylboronic acids or arylborates, which are readily accessible by lithiation of aryl bromides followed by treatment with trimethoxyborane, with α,β-unsaturated esters in the presence of rhodium/(S)-binap catalyst proceeded with high enantioselectivity to give high yields of optically active β-aryl esters of up to 98% ee. The enantioselectivity depends on the steric bulkiness

  芳基硼试剂，芳基硼酸或芳基硼酸酯的反应很容易通过芳基溴化物的锂化反应，然后在铑/（S）-双键催化剂存在下用三甲氧基硼烷与α，β-不饱和酯进行处理，以高对映选择性进行，得到高达98％ee的高光学活性β-芳基酯收率。对映选择性取决于酯部分的空间体积。
• Asymmetric 1,4-addition of aryltrialkoxysilanes to α,β-unsaturated esters and amides catalyzed by a chiral rhodium complex
  作者：Shuichi Oi、Akio Taira、Yoshio Honma、Takashi Sato、Yoshio Inoue

  DOI：10.1016/j.tetasy.2005.12.032

  日期：2006.2

  A highly enantioselective 1,4-addition of aryltrialkoxysilanes to α,β-unsaturated esters and amides was successfully catalyzed by a chiral rhodium complex generated from [Rh(cod)(MeCN)2]BF4 and (S)-BINAP.

  由[Rh（cod）（MeCN）2 ] BF 4和（S）-BINAP生成的手性铑配合物成功地催化了芳基三烷氧基硅烷与α，β-不饱和酯和酰胺的高对映选择性的1,4-加成反应。
• Applications of 4,4‘-(Me₃Si)₂-BINAP in Transition-Metal-Catalyzed Asymmetric Carbon−Carbon Bond-Forming Reactions
  作者：Masamichi Ogasawara、Helen L. Ngo、Takeshi Sakamoto、Tamotsu Takahashi、Wenbin Lin

  DOI：10.1021/ol050834s

  日期：2005.7.1

  A recently developed BINAP derivative with trimethylsilyl substituents on the 4- and 4 '-positions of the binaphthyl skeleton, 2,2 '-bis-(diphenylphosphino)-4,4 '-bis(trimethylsilyl)-1,1 '-binaphthyl (tms-BINAP), was used in a variety of transition-metal-catalyzed asymmetric carbon-carbon bond-forming reactions. In pi-allylpalladium-mediated reactions, tms-BINAP gave better enantioselectivity than the unsubstituted BINAP, and the origin of the improved enantioselectivity was gained from an X-ray structural study of [Pd(eta(3)-C3H5)((R)-tms-BINAP)]CIO4.