benzyl ((diethoxyphosphoryl)(phenyl)methyl)carbamate | 67564-53-8

• 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: benzyl ((diethoxyphosphoryl)(phenyl)methyl)carbamate
• 英文别名: benzyl N-[(R)-[diethoxy(oxido)phosphaniumyl]-phenylmethyl]carbamate
• CAS: 67564-53-8
• 化学式: C₁₉H₂₄NO₅P
• 分子量: 377.377
• InChiKey: NRVOVHDHRBMPJU-GOSISDBHSA-N

物化性质

• 沸点：
  533.9±50.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-[(3aR,7aR)-2-oxido-1,3-di(propan-2-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-ium-2-yl]-1-phenylmethanimine 在 盐酸 、 水 、 碳酸氢钠 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 benzyl ((diethoxyphosphoryl)(phenyl)methyl)carbamate
  参考文献：
  名称：

  Research Article: Asymmetric Hydrophosphylation of Chiral N-Phosphonyl Imines Provides an Efficient Approach to Chiral α-Amino Phosphonates

  摘要：

  Chiral N‐phosphonylimines were found to react with lithium phosphites to provide various substituted chiral α‐amino phosphonates in excellent yields (94–97%) and diastereoselectivities (93:7–99:1). The types of bases utilized for generating the nucleophile are crucial for the effectiveness of asymmetric induction. In addition, N,N‐isopropyl group on chiral N‐phosphonylimine auxilliary was proven to be superior to other protecting groups in controlling diastereoselectivity. The absolute configuration was unambiguously determined by converting a chiral α‐amino phosphonate into its authentic N‐Cbz derivative.

  DOI：

  10.1111/j.1747-0285.2010.01013.x

文献信息

• Enantioselective hydrophosphonylation of <i>N</i>-Boc imines using chiral guanidine–thiourea catalysts
  作者：Louis Chassillan、Yasuhiro Yamashita、Woo-Jin Yoo、Martial Toffano、Régis Guillot、Shū Kobayashi、Giang Vo-Thanh

  DOI：10.1039/d1ob01953h

  日期：——

  The enantioselective hydrophosphonylation of N-Boc imines was investigated using a new family of pseudo-symmetric guanidine–thiourea catalysts, providing α-amino phosphonates in moderate to high yields with good enantioselectivity. The catalyst was heterogenized by polymerization with styrene and the resulting catalyst was applied to reactions under continuous-flow conditions.

  N -Boc 亚胺的对映选择性氢化膦酰化研究使用一类新的假对称胍-硫脲催化剂，以中等至高产率提供具有良好对映选择性的 α-氨基膦酸盐。通过与苯乙烯聚合使催化剂异质化，并将所得催化剂应用于连续流动条件下的反应。
• Research Article: Asymmetric Hydrophosphylation of Chiral N-Phosphonyl Imines Provides an Efficient Approach to Chiral α-Amino Phosphonates
  作者：Parminder Kaur、Walter Wever、Trideep Rajale、Guigen Li

  DOI：10.1111/j.1747-0285.2010.01013.x

  日期：2010.10

  Chiral N‐phosphonylimines were found to react with lithium phosphites to provide various substituted chiral α‐amino phosphonates in excellent yields (94–97%) and diastereoselectivities (93:7–99:1). The types of bases utilized for generating the nucleophile are crucial for the effectiveness of asymmetric induction. In addition, N,N‐isopropyl group on chiral N‐phosphonylimine auxilliary was proven to be superior to other protecting groups in controlling diastereoselectivity. The absolute configuration was unambiguously determined by converting a chiral α‐amino phosphonate into its authentic N‐Cbz derivative.