2-[(4R)-4-异丙基-4,5-二氢-1,3-恶唑-2-基]-2-丙醇 | 245503-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 2-[(4R)-4-异丙基-4,5-二氢-1,3-恶唑-2-基]-2-丙醇
• 中文别名: 甲基三(3-苯基丙氧基)硅烷
• 英文名称: (R)-4,5-dihydro-α,α-dimethyl-4-isopropyloxazole-2-ethanol
• 英文别名: (R)-2-(4-Isopropyl-4,5-dihydrooxazol-2-yl)propan-2-ol；2-[(4R)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-ol
• CAS: 245503-15-5
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: MSUGQGACPOZSJS-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4R)-4-异丙基-4,5-二氢-1,3-恶唑-2-基]-2-丙醇 、 (3aR,8aR)-6-Chloro-2,2-dimethyl-4,4,8,8-tetra-naphthalen-2-yl-tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3aR,8aR)-6-{1-[(4R)-4,5-dihydro-4-isopropyloxazol-2-yl]-1-methylethoxy}-3a,4,8,8a-tetrahydro-4,4,8,8-tetra(naphthalen-2-yl)-1,3,5,7-tetraoxa-6-phosphazulene
  参考文献：
  名称：

  Catalytic Enantioselective Hydrosilylation of Ketones with Rhodium-Phosphite Complexes Containing a TADDOLate and a Dihydrooxazole Unit

  摘要：

  New types of chiral phosphorus/nitrogen ligands, capable of forming six-membered-ring metal chelates have been prepared from alpha,alpha,alpha',alpha'-tetraaryl-1,2-dioxolane-4,5-dimethanols (TADDOLs), PCl3, and dihydrooxazole alcohols (from amino acids) (7 in Scheme 1). The X-ray crystal structure of a Rh complex of one of these ligands, 8b, has been determined (Scheme 2 and Fig.). Enantioselective hydrosilylations of dialkyl and aryl alkyl ketones with Ph2SiH2/0.01 equiv. Rh-1.7 have been studied and found to provide secondary alcohols in enantiomer ratios of up to 97: 3 (Scheme 3 and Table). The ligand prepared from (R,R)-TADDOL and the (R)-valine-derived (R)-alpha,alpha-dimethyl-4-isopropyl-4,5-dihydro gives better results than the (R,R,S)-isomer (7d vs. 7c in Scheme 3), and an i-Pr group on the 4,5-dihydrooxazole ring gives rise to a slightly better selectivity than a Ph group. With the (R,R,R)-ligands the hydrogen transfer occurs from the Re face of the oxo groups (Sclleme 4).

  DOI：

  10.1002/(sici)1522-2675(19990707)82:7<1096::aid-hlca1096>3.0.co;2-i
• 作为产物：
  描述：

  D-缬氨醇 、 2-甲基-2-羟基丙酸 以 xylene 为溶剂， 反应 30.0h， 以31%的产率得到2-[(4R)-4-异丙基-4,5-二氢-1,3-恶唑-2-基]-2-丙醇
  参考文献：
  名称：

  Catalytic Enantioselective Hydrosilylation of Ketones with Rhodium-Phosphite Complexes Containing a TADDOLate and a Dihydrooxazole Unit

  摘要：

  New types of chiral phosphorus/nitrogen ligands, capable of forming six-membered-ring metal chelates have been prepared from alpha,alpha,alpha',alpha'-tetraaryl-1,2-dioxolane-4,5-dimethanols (TADDOLs), PCl3, and dihydrooxazole alcohols (from amino acids) (7 in Scheme 1). The X-ray crystal structure of a Rh complex of one of these ligands, 8b, has been determined (Scheme 2 and Fig.). Enantioselective hydrosilylations of dialkyl and aryl alkyl ketones with Ph2SiH2/0.01 equiv. Rh-1.7 have been studied and found to provide secondary alcohols in enantiomer ratios of up to 97: 3 (Scheme 3 and Table). The ligand prepared from (R,R)-TADDOL and the (R)-valine-derived (R)-alpha,alpha-dimethyl-4-isopropyl-4,5-dihydro gives better results than the (R,R,S)-isomer (7d vs. 7c in Scheme 3), and an i-Pr group on the 4,5-dihydrooxazole ring gives rise to a slightly better selectivity than a Ph group. With the (R,R,R)-ligands the hydrogen transfer occurs from the Re face of the oxo groups (Sclleme 4).

  DOI：

  10.1002/(sici)1522-2675(19990707)82:7<1096::aid-hlca1096>3.0.co;2-i

文献信息

• Catalytic Enantioselective Hydrosilylation of Ketones with Rhodium-Phosphite Complexes Containing a TADDOLate and a Dihydrooxazole Unit
  作者：Dieter K. Heldmann、Dieter Seebach

  DOI：10.1002/(sici)1522-2675(19990707)82:7<1096::aid-hlca1096>3.0.co;2-i

  日期：1999.7.7

  New types of chiral phosphorus/nitrogen ligands, capable of forming six-membered-ring metal chelates have been prepared from alpha,alpha,alpha',alpha'-tetraaryl-1,2-dioxolane-4,5-dimethanols (TADDOLs), PCl3, and dihydrooxazole alcohols (from amino acids) (7 in Scheme 1). The X-ray crystal structure of a Rh complex of one of these ligands, 8b, has been determined (Scheme 2 and Fig.). Enantioselective hydrosilylations of dialkyl and aryl alkyl ketones with Ph2SiH2/0.01 equiv. Rh-1.7 have been studied and found to provide secondary alcohols in enantiomer ratios of up to 97: 3 (Scheme 3 and Table). The ligand prepared from (R,R)-TADDOL and the (R)-valine-derived (R)-alpha,alpha-dimethyl-4-isopropyl-4,5-dihydro gives better results than the (R,R,S)-isomer (7d vs. 7c in Scheme 3), and an i-Pr group on the 4,5-dihydrooxazole ring gives rise to a slightly better selectivity than a Ph group. With the (R,R,R)-ligands the hydrogen transfer occurs from the Re face of the oxo groups (Sclleme 4).