(E,2R,3S)-1-[(3aR,8bS)-2-sulfanylidene-4,8b-dihydro-3aH-indeno[1,2-d][1,3]thiazol-1-yl]-3-hydroxy-2-methyl-5-phenylpent-4-en-1-one | 1009061-76-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E,2R,3S)-1-[(3aR,8bS)-2-sulfanylidene-4,8b-dihydro-3aH-indeno[1,2-d][1,3]thiazol-1-yl]-3-hydroxy-2-methyl-5-phenylpent-4-en-1-one
• CAS: 1009061-76-0
• 化学式: C₂₂H₂₁NO₂S₂
• 分子量: 395.546
• InChiKey: INLHFAGVBSKSIQ-OEUPYIERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,2R,3S)-1-[(3aR,8bS)-2-sulfanylidene-4,8b-dihydro-3aH-indeno[1,2-d][1,3]thiazol-1-yl]-3-hydroxy-2-methyl-5-phenylpent-4-en-1-one 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以73%的产率得到(2R,3S)-3-hydroxy-2-methyl-5-phenyl-pent-4-enoic acid
  参考文献：
  名称：

  Indene-Based Thiazolidinethione Chiral Auxiliary for Propionate and Acetate Aldol Additions

  摘要：

  An indene-based thiazolidinethione chiral auxiliary was prepared in two steps from trans-1-amino-2-indanol. Chlorotitanium enolates of this chiral auxiliary delivered excellent diastereoselectivities in propionate and acetate aldol additions. The chiral auxiliary was easily removed to deliver several valuable functionalities.

  DOI：

  10.1021/ol702980p
• 作为产物：
  描述：

  反式肉桂醛 、 3-((4S,5R)-indano[1,2-d]thiazolidin-2-thione)-propan-1-one 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到(E,2R,3S)-1-[(3aR,8bS)-2-sulfanylidene-4,8b-dihydro-3aH-indeno[1,2-d][1,3]thiazol-1-yl]-3-hydroxy-2-methyl-5-phenylpent-4-en-1-one
  参考文献：
  名称：

  Indene-Based Thiazolidinethione Chiral Auxiliary for Propionate and Acetate Aldol Additions

  摘要：

  An indene-based thiazolidinethione chiral auxiliary was prepared in two steps from trans-1-amino-2-indanol. Chlorotitanium enolates of this chiral auxiliary delivered excellent diastereoselectivities in propionate and acetate aldol additions. The chiral auxiliary was easily removed to deliver several valuable functionalities.

  DOI：

  10.1021/ol702980p

文献信息

• Indene-Based Thiazolidinethione Chiral Auxiliary for Propionate and Acetate Aldol Additions
  作者：Antonio Osorio-Lozada、Horacio F. Olivo

  DOI：10.1021/ol702980p

  日期：2008.2.1

  An indene-based thiazolidinethione chiral auxiliary was prepared in two steps from trans-1-amino-2-indanol. Chlorotitanium enolates of this chiral auxiliary delivered excellent diastereoselectivities in propionate and acetate aldol additions. The chiral auxiliary was easily removed to deliver several valuable functionalities.