cis 1-phenyl-1,2,3,4-tetrahydro-2-naphthaleneacetic acid methyl ester | 135107-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: cis 1-phenyl-1,2,3,4-tetrahydro-2-naphthaleneacetic acid methyl ester
• 英文别名: methyl 2-[(1S,2S)-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]acetate
• CAS: 135107-85-6
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: RJKXANGMEGTSQG-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  1,2,3,4-四氢-1-氧代-2-萘乙酸甲酯 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 cis 1-phenyl-1,2,3,4-tetrahydro-2-naphthaleneacetic acid methyl ester
  参考文献：
  名称：

  Arylmagnesium bromide additions to 1-tetralone-2-acetic acid followed by catalytic hydrogenolysis: stereochemical consequences

  摘要：

  A Stork reaction route (7 --> 1b) was utilized to synthesize 1-tetralone-2-acetic acid methyl ester (1a) from 1-tetralone. Addition of a 2'-(o-methoxyphenyl) magnesium bromide to this ketone followed by palladium-catalyzed hydrogenation of the intermediate cis lactones (2, verified by X-ray crystal structure determination of 2a, Figure 1), afforded predominantly a 1,2-cis tetralin (3) accompanied by smaller yields of the corresponding 1,2-trans tetralin (4). The stereochemical consequences of this reaction sequence was unequivocally established by X-ray crystal structure elucidation of 1,2-cis methyl ester 3b (Figure 2) and 1,2-trans carboxylic acid 4a (Figure 3). Stereochemical assignments for the analogous diastereoisomeric sets 3c-f and 4c-f were obtained by high-field (400-MHz) H-1 and C-13 NMR correlations with the crystal structures. The overall reaction pathway illustrates a useful approach to 1,2-cis-alkylated tetralins and certain sterically hindered 1,2-trans-alkylated tetralins.

  DOI：

  10.1021/jo00018a030

文献信息

• Arylmagnesium bromide additions to 1-tetralone-2-acetic acid followed by catalytic hydrogenolysis: stereochemical consequences
  作者：Carl Djerassi、George R. Pettit、Delbert L. Herald、Dale R. Sanson

  DOI：10.1021/jo00018a030

  日期：1991.8

  A Stork reaction route (7 --> 1b) was utilized to synthesize 1-tetralone-2-acetic acid methyl ester (1a) from 1-tetralone. Addition of a 2'-(o-methoxyphenyl) magnesium bromide to this ketone followed by palladium-catalyzed hydrogenation of the intermediate cis lactones (2, verified by X-ray crystal structure determination of 2a, Figure 1), afforded predominantly a 1,2-cis tetralin (3) accompanied by smaller yields of the corresponding 1,2-trans tetralin (4). The stereochemical consequences of this reaction sequence was unequivocally established by X-ray crystal structure elucidation of 1,2-cis methyl ester 3b (Figure 2) and 1,2-trans carboxylic acid 4a (Figure 3). Stereochemical assignments for the analogous diastereoisomeric sets 3c-f and 4c-f were obtained by high-field (400-MHz) H-1 and C-13 NMR correlations with the crystal structures. The overall reaction pathway illustrates a useful approach to 1,2-cis-alkylated tetralins and certain sterically hindered 1,2-trans-alkylated tetralins.