(4S,5S)-3-(9-Bora-bicyclo[3.3.1]non-9-yl)-2-[1-chloro-meth-(Z)-ylidene]-4-methoxymethyl-5-phenyl-oxazolidine | 252880-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: (4S,5S)-3-(9-Bora-bicyclo[3.3.1]non-9-yl)-2-[1-chloro-meth-(Z)-ylidene]-4-methoxymethyl-5-phenyl-oxazolidine
• 英文别名: (2Z,4S,5S)-3-(9-borabicyclo[3.3.1]nonan-9-yl)-2-(chloromethylidene)-4-(methoxymethyl)-5-phenyl-1,3-oxazolidine
• CAS: 252880-50-5
• 化学式: C₂₀H₂₇BClNO₂
• 分子量: 359.704
• InChiKey: NXBZKFJIPZBFLS-PXUQNWAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-3-(9-Bora-bicyclo[3.3.1]non-9-yl)-2-[1-chloro-meth-(Z)-ylidene]-4-methoxymethyl-5-phenyl-oxazolidine 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-2,2-bis(4-methoxyphenyl)ethanone
  参考文献：
  名称：

  Boron azaenolates of chiral oxazolines: synthesis of optically active formyl oxiranes

  摘要：

  Boron azaenolates 2 and 8 from the optically active chloromethyloxazolines 1 and 7 have been found to couple with ketones in a highly diastereoselective fashion, which depends markedly upon the geometry (Z) of the azaenolates and the nature of the ligands which are present on the boron atom, in good accordance with semiempirical calculations (AM1). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01480-x
• 作为产物：
  描述：

  (4S,5S)-(-)-4-甲氧甲基-2-甲基-5-苯基-2-恶唑啉 在 三乙胺 作用下， 反应 1.0h， 生成 (4S,5S)-3-(9-Bora-bicyclo[3.3.1]non-9-yl)-2-[1-chloro-meth-(Z)-ylidene]-4-methoxymethyl-5-phenyl-oxazolidine
  参考文献：
  名称：

  从手性2-氯甲基恶唑啉的氮杂酸酯类高度立体选择性合成旋光性恶唑啉基恶唑烷

  摘要：

  发现旋光性氯甲基恶唑啉1分别在0°C和-100°C生成的硼和氮杂钛酸2和4与脂族酮以非对映选择性的方式偶合，最终形成旋光性恶唑啉基肟3。较少的立体选择性是与芳族酮的反应。

  DOI：

  10.1016/s0040-4039(00)00809-1

文献信息

• Azaenolates of 2-Chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline − A Highly Diastereo- and Enantioselective Synthesis of Oxazolinyloxiranes
  作者：Vito Capriati、Saverio Florio、Renzo Luisi

  DOI：10.1002/1099-0690(200106)2001:11<2035::aid-ejoc2035>3.0.co;2-r

  日期：2001.6

  The oxazoline-derived titanium azaenolate 6 couples highly stereoselectively with aldehydes affording highly optically pure oxazolinyloxiranes 7. The epoxide 7a has been deblocked to form the optically pure formyl oxirane 9. In contrast, the corresponding boron azaenolates 2 and 3 couple with very poor or no stereoselectivity. Lithium, aluminum and tin azaenolates have also been shortly studied.
• Boron azaenolates of chiral oxazolines: synthesis of optically active formyl oxiranes
  作者：Saverio Florio、Vito Capriati、Renzo Luisi、Alessandro Abbotto

  DOI：10.1016/s0040-4039(99)01480-x

  日期：1999.10

  Boron azaenolates 2 and 8 from the optically active chloromethyloxazolines 1 and 7 have been found to couple with ketones in a highly diastereoselective fashion, which depends markedly upon the geometry (Z) of the azaenolates and the nature of the ligands which are present on the boron atom, in good accordance with semiempirical calculations (AM1). (C) 1999 Elsevier Science Ltd. All rights reserved.
• Highly stereoselective synthesis of optically active oxazolinyl oxiranes from azaenolates of a chiral 2-chloromethyloxazoline
  作者：Saverio Florio、Vito Capriati、Renzo Luisi

  DOI：10.1016/s0040-4039(00)00809-1

  日期：2000.7

  Boron and titanium azaenolates 2 and 4, generated at 0°C and −100°C, respectively, from the optically active chloromethyloxazoline 1, have been found to couple with aliphatic ketones in a highly diastereoselective fashion ending up with the formation of optically active oxazolinyl oxiranes 3. Less stereoselective was the reaction with aromatic ketones.

  发现旋光性氯甲基恶唑啉1分别在0°C和-100°C生成的硼和氮杂钛酸2和4与脂族酮以非对映选择性的方式偶合，最终形成旋光性恶唑啉基肟3。较少的立体选择性是与芳族酮的反应。