tert-butyl (E,2R,3S)-6-[(3aR,7aR)-1,3-dimethyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-2-methyl-3-phenylhex-5-enoate | 150932-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (E,2R,3S)-6-[(3aR,7aR)-1,3-dimethyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-2-methyl-3-phenylhex-5-enoate
• CAS: 150932-52-8
• 化学式: C₂₅H₃₉N₂O₃P
• 分子量: 446.57
• InChiKey: FFNGBAOXSYLYTJ-IDAOXTJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (E,2R,3S)-6-[(3aR,7aR)-1,3-dimethyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-2-methyl-3-phenylhex-5-enoate 在 臭氧 作用下， 生成 (2R,3S)-5-Hydroxy-2-methyl-3-phenyl-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric conjugate additions of chiral allyl- and crotylphosphonamide anions to .alpha.,.beta.-unsaturated carbonyl compounds: highly stereocontrolled access to vicinally substituted carbon centers and chemically asymmetrized chirons

  摘要：

  Reactions of anions derived from chiral nonracemic allyl and crotyl bicyclic phosphonamides with alpha,beta-unsaturated cyclic ketones, esters, lactones, and lactams take place at the gamma-position of the reagents and lead to diastereomerically pure or highly enriched products of conjugate addition. The option to quench the corresponding enolates with various alkyl halides offers a versatile approach to vicinal substitution including the generation of quaternary carbon centers.

  DOI：

  10.1021/jo00071a004
• 作为产物：
  描述：

  肉桂酸椒丁酯 、 (3aR,7aR)-2-allyloctahydro-1H-1,3-dimethyl-1,3,2-benzadiazaphosphole 2-oxide 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以50%的产率得到tert-butyl (E,2R,3S)-6-[(3aR,7aR)-1,3-dimethyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-2-methyl-3-phenylhex-5-enoate
  参考文献：
  名称：

  手性膦酰胺阴离子向α，β-不饱和羰基化合物的不对称共轭加成。一种通用的方法来取代毒substituted

  摘要：

  衍生自手性非外消旋烯丙基，巴豆基和肉桂基双环C（2）对称膦酰胺的阴离子与α，β-不饱和环酮，酯，内酯和内酰胺的反应在试剂的γ位发生。产物是非对映体纯的或富集的β-取代的羰基化合物。该方法还可以轻松地以一锅序列的方式多达三个立体定位中心的邻近取代，在某些情况下还包括季碳原子。

  DOI：

  10.1021/jo000388g

文献信息

• Asymmetric Conjugate Additions of Chiral Phosphonamide Anions to α,β-Unsaturated Carbonyl Compounds. A Versatile Method for Vicinally Substituted Chirons
  作者：Stephen Hanessian、Arthur Gomtsyan、Nadia Malek

  DOI：10.1021/jo000388g

  日期：2000.9.1

  Reactions of anions derived from chiral nonracemic allyl, crotyl, and cinnamyl bicyclic C(2)-symmetrical phosphonamides with alpha, beta-unsaturated cyclic ketones, esters, lactones, and lactams take place at the gamma-position of the reagents. The products are diastereomerically pure or enriched beta-substituted carbonyl compounds. The method also provides easy access to vicinal substitution of as

  衍生自手性非外消旋烯丙基，巴豆基和肉桂基双环C（2）对称膦酰胺的阴离子与α，β-不饱和环酮，酯，内酯和内酰胺的反应在试剂的γ位发生。产物是非对映体纯的或富集的β-取代的羰基化合物。该方法还可以轻松地以一锅序列的方式多达三个立体定位中心的邻近取代，在某些情况下还包括季碳原子。
• Asymmetric conjugate additions of chiral allyl- and crotylphosphonamide anions to .alpha.,.beta.-unsaturated carbonyl compounds: highly stereocontrolled access to vicinally substituted carbon centers and chemically asymmetrized chirons
  作者：Stephen Hanessian、Arthur Gomtsyan、Andrew Payne、Yolande Herve、Serge Beaudoin

  DOI：10.1021/jo00071a004

  日期：1993.9

  Reactions of anions derived from chiral nonracemic allyl and crotyl bicyclic phosphonamides with alpha,beta-unsaturated cyclic ketones, esters, lactones, and lactams take place at the gamma-position of the reagents and lead to diastereomerically pure or highly enriched products of conjugate addition. The option to quench the corresponding enolates with various alkyl halides offers a versatile approach to vicinal substitution including the generation of quaternary carbon centers.