(1Z)-1-(benzyloxymethyloxy)-3-cyclohexyl-4-hydroxy-1-decene | 133210-34-1

• 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: (1Z)-1-(benzyloxymethyloxy)-3-cyclohexyl-4-hydroxy-1-decene
• 英文别名: (Z,3R,4R)-3-cyclohexyl-1-(phenylmethoxymethoxy)dec-1-en-4-ol
• CAS: 133210-34-1；133210-37-4；133210-40-9；143765-19-9；143765-21-3
• 化学式: C₂₄H₃₈O₃
• 分子量: 374.564
• InChiKey: WSYJPEUXNALESM-LWACLWBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  27.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  庚醛 、 (2E)-1-(Benzyloxymethyloxy)-3-(cyclohexyl)-2-propenyl(tri-n-butyl)stannane 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (1Z)-1-(benzyloxymethyloxy)-3-cyclohexyl-4-hydroxy-1-decene 、 (1E)-1-(benzyloxymethyloxy)-3-cyclohexyl-4-hydroxy-1-decene 、 (Z)-(3R,4S)-1-Benzyloxymethoxy-3-cyclohexyl-dec-1-en-4-ol
  参考文献：
  名称：

  Evidence for Synclinal Transition State in the Reactions of Aromatic Aldehydes with α-(Alkoxy)allylstannanes

  摘要：

  Unlike aliphatic aldehydes, aromatic aldehydes produce greater than 95% of syn-(Z) enol ether when treated with alpha-(alkoxy)allylstannanes in the presence of BF3.Et2O. However, in the presence of TiCl4, the reaction of p-chloro-o-methoxybenzaldehyde with alpha-(alkoxy)crotylstannane produced predominantly the syn-(E) isomer.

  DOI：

  10.1016/s0040-4020(01)88299-5

文献信息

• Remarkable increase in the diastereofacial selectivity of the addition of β-methyl α-(alkoxy)allylstannane to aldehydes: substituent effects on diastereofacial selectivity
  作者：Benjamin W Gung、Daniel T Smith、Mark A Wolf

  DOI：10.1016/s0040-4039(00)71205-6

  日期：1991.1

  Several new chiral allylstannanes were prepared and reacted with aldehydes. Excellent diastereofacial selectivity was observed for the reactions of allylstannane 1 with aldehydes in the presence of BF3·Et2O. This is in contrast to the results from other allylstannanes which do not bear a β-methyl group. These observations were rationalized based on a combination of steric and electronic effects.

  制备了几种新的手性烯丙基锡烷，并与醛反应。在存在BF 3 ·Et 2 O的情况下，烯丙基锡烷1与醛的反应具有极好的非对映选择性，这与其他不带有β-甲基基团的烯丙基锡的结果相反。这些观察是基于空间和电子效应的组合而合理化的。