(S)-2-羟基-2-甲基己醛 | 121222-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-2-羟基-2-甲基己醛
• 英文名称: (S)-2-Hydroxy-2-methyl-hexanal
• 英文别名: (2S)-2-hydroxy-2-methylhexanal
• CAS: 121222-01-3
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: UZFZXFNCUUULCV-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-羟基-2-甲基己醛 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 以65%的产率得到(-)(2S)-2-methyl-2-hydroxy-1-hexanol
  参考文献：
  名称：

  Synthèse efficace des méthyl-2 hexanediols-1,2 optiquement actifs

  摘要：

  DOI：

  10.1016/s0040-4039(00)80806-0
• 作为产物：
  描述：

  (1S,3S,7S,9R,1′S)-5-(2′-hydroxyhex-2′-yl)-10,10-dimethyl-3-phenyl-4,6-dioxatricyclo[7.1.1.0^2,7]undecane 在 水 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 (S)-2-羟基-2-甲基己醛
  参考文献：
  名称：

  Nucleophilic additions on acetyldioxanes derived from (−)-(1 R )-myrtenal used as chiral auxiliaries: substituent effects on the stereochemical outcome

  摘要：

  The synthesis of acetyldioxanes 4 and 9a starting from (-)-(1R)-myrtenal is described. The products were treated with a representative series of nucleophilic reagents (RMgX, RLi, NaBH4 and LiAlH4) to assess the effect of the substituent at C-3 on the stereochemical outcome. It was observed that the nucleophiles preferred the re -face of the C=O group when the equatorial substituent at C-3 was a methyl group, whereas a phenyl group at the same position induced the addition through the si-face, thus allowing access to either desired stereochemistry of a final product. This behavior suggests that the formation of the expected Cram-chelated coordination complex takes a coplanar orientation with the C-3 equatorial substituent. Moreover, Grignard reagents were the most stereoselective nucleophiles. The stereochemistry of the addition was established by X-ray diffraction and chemical correlation. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.07.008

文献信息

• CERVANTES-CUEVAS, HUMBERTO;JOSEPH-NATHAN, PEDRO, TETRAHEDRON LETT., 29,(1988) N 43, C. 5535-5536
  作者：CERVANTES-CUEVAS, HUMBERTO、JOSEPH-NATHAN, PEDRO

  DOI：——

  日期：——