N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane | 226067-50-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane
• 英文别名: N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane；(2R,3S)-2-bromo-1-[(1S,5R,7R)-10,10-dimethyl-3-sulfanylidene-4-oxa-2-azatricyclo[5.2.1.01,5]decan-2-yl]-3-hydroxy-3-phenylpropan-1-one
• CAS: 226067-50-1
• 化学式: C₁₉H₂₂BrNO₃S
• 分子量: 424.359
• InChiKey: ROHARRVQVVKZIZ-DQQFRQOVSA-N

物化性质

• 沸点：
  498.9±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  An efficient method for the synthesis of enantiopure cis-α,β-epoxy acids

  摘要：

  Enantiopure cis-alpha,beta-epoxy acids were prepared via a modified Darzen's reaction employing the titanium-mediated bromination-aldolization of chiral acetate thioimide enolate. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00320-1
• 作为产物：
  描述：

  苯甲醛 、 N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane 在 溴 、 四氯化钛 、 N,N-二异丙基乙胺 作用下， 生成 N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane
  参考文献：
  名称：

  衍生自硫酰亚胺的手性乙酸烯醇钛酸酯的不对称溴化-醛醇缩合。合成对映纯α-溴-β-羟基羧酸的一般方法

  摘要：

  衍生自硫酰亚胺的手性乙酸烯醇钛酸酯可有效完成一步溴化-醛缩醛化反应，并具有优异的收率，并且在添加醛醇缩合剂时异常高的不对称诱导率。一般的碱促进的恶唑烷硫酮脱酰作用可直接获得手性α-溴-β-羟基酸。

  DOI：

  10.1016/s0040-4039(99)00576-6

文献信息

• Asymmetric bromination-aldolization of chiral acetate titanium enolate derived from thioimide. A general approach to the synthesis of enantiopure α-bromo-β-hydroxy carboxylic acids
  作者：Ying-Chuan Wang、Dah-Wei Su、Chen-Men Lin、Hsi-Liang Tseng、Chi-Lung Li、Tu-Hsin Yan

  DOI：10.1016/s0040-4039(99)00576-6

  日期：1999.4

  Chiral acetate titanium enolate derived from thioimide efficiently effects one-step bromination-aldolization with excellent yields and exceptionally high levels of asymmetric induction in aldol additions. General base promoted oxazolidinethione deacylation provides direct access to chiral α-bromo-β-hydroxy acids.

  衍生自硫酰亚胺的手性乙酸烯醇钛酸酯可有效完成一步溴化-醛缩醛化反应，并具有优异的收率，并且在添加醛醇缩合剂时异常高的不对称诱导率。一般的碱促进的恶唑烷硫酮脱酰作用可直接获得手性α-溴-β-羟基酸。
• Toward the Development of a General Chiral α-Substituted Acetate Enolate Synthon for Aldolization. DMAP- and NEt₃-Promoted Oxazolidinethione “Deacylation”
  作者：Ying-Chuan Wang、Dah-Wei Su、Chen-Men Lin、Hsi-Liang Tseng、Chi-Lung Li、Tu-Hsin Yan

  DOI：10.1021/jo990444h

  日期：1999.8.1
• A facile method for the synthesis of enantiopure α-unsubstituted β-hydroxy esters
  作者：Ying-Chuan Wang、Jia-Yang Hwang、Yih-Cheng Chen、Shang-Chi Chuang、Tu-Hsin Yan

  DOI：10.1016/s0957-4166(00)00109-9

  日期：2000.5

  One-pot deacylation-debromination reactions involving the transesterification of the initial chiral beta-bromo-beta-hydroxy thioimide aldol adducts and subsequent Al-Hg mediated reductive cleavage of the C-Br bond allow for a facile synthesis of enantiopure beta-hydroxy esters. (C) 2000 Published by Elsevier Science Ltd.
• A New Approach for the Chemoselective Debromination of Chiral Bromohydrins. Toward the Development of a Very General Approach to Enantiopure α-Unsubstituted β-Hydroxy Acids
  作者：Ying-Chuan Wang、Tu-Hsin Yan

  DOI：10.1021/jo000124u

  日期：2000.10.1
• An efficient method for the synthesis of enantiopure cis-α,β-epoxy acids
  作者：Ying-Chuan Wang、Chi-Lung Li、Hsi-Liang Tseng、Shang-Chi Chuang、Tu-Hsin Yan

  DOI：10.1016/s0957-4166(99)00320-1

  日期：1999.8

  Enantiopure cis-alpha,beta-epoxy acids were prepared via a modified Darzen's reaction employing the titanium-mediated bromination-aldolization of chiral acetate thioimide enolate. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.