(1S,3S)-3-amino-1,3-diphenylpropan-1-ol | 873695-73-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1S,3S)-3-amino-1,3-diphenylpropan-1-ol
• 英文别名: (1S,3S)-3-amino-1,3-diphenyl-propan-1-ol；(1S,3S)-3-Amino-1,3-diphenyl-propan-1-ol
• CAS: 873695-73-9
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: HQFWJAGMDNUMAK-GJZGRUSLSA-N

物化性质

• 沸点：
  395.3±30.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 (1S,3S)-3-amino-1,3-diphenylpropan-1-ol 在 sodium hydroxide 作用下， 生成 rac-(1S,3S)-3-benzoylamino-1,3-diphenyl-1-propanol
  参考文献：
  名称：

  Pulmonary cryptococcosis and Capillaria aerophila infection in an FIV-positive cat

  摘要：

  A 12‐year‐old, FIV‐positive, domestic longhair cat was presented with a history of sneezing and coughing during the previous seven months. On thoracic radiographs, a prominent bronchial pattern and three focal, opacified nodules were seen. Cytology of bronchoalveolar lavage fluid demonstrated spherical, capsulate, narrow‐necked, budding yeasts within macrophages. Culture of the fluid yielded a heavy growth of Cryptococcus neoformans var neoformans. The serum latex cryptococcal antigen agglutination test titre was 158. The cat was treated with itraconazole and the cough resolved over a 5‐month period but then recurred. Repeat thoracic radiographs showed resolution of the pulmonary nodules but a persistent bronchial pattern. Adult nematodes and ova with morphology characteristic of Capillaria aerophila were seen in bronchoalveolar lavage fluid and no yeasts were cultured from the fluid. The cryptococcal titre was zero. The lungworm infection was treated successfully with abamectin and the cough resolved. Immunosuppression related to FIV infection may have predisposed this cat to sequential respiratory tract infections.

  DOI：

  10.1111/j.1751-0813.2000.tb10581.x
• 作为产物：
  描述：

  benzaldehyde N-boc imine 在 六甲基磷酰三胺 、 bis(2-methoxyethyl) azodicarboxylate 、 samarium diiodide 、 二苯基-2-吡啶膦 、 (R)-3,3'-di(4-tert-butylphenyl)(1,1'-binaphthyl)-2,2'-disulfonic acid 、 potassium tert-butylate 、 magnesium ethylate 、 sodium hydride 、 caesium carbonate 、 三乙胺 、 molybdenum hexacarbonyl 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二乙醚 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 43.5h， 生成 (1S,3S)-3-amino-1,3-diphenylpropan-1-ol
  参考文献：
  名称：

  手性镁盐联萘二甲酸二磺酸钾簇合物手性布朗斯台德酸催化剂催化苯乙烯与醛亚胺的对映选择性环加成反应

  摘要：

  手性双萘基二磺酸镁钾盐簇，作为手性布朗斯台德酸催化剂，首次显示出与醛亚胺催化苯乙烯的对映选择性环加成反应。催化剂前体的强布朗斯台德酸度可能会溶解干燥剂并吸收浸出的Mg 2+和K +，从而偶然产生了良好的对映选择性。催化剂的X射线和ESI-MS分析以及反应动力学研究为力学方面提供了支持。还证实了以克为单位的向光学活性的1，3-氨基醇的有用转化。

  DOI：

  10.1021/jacs.7b04795

文献信息

• Asymmetric Aza-Mannich Reactions of Sulfinimines:  Scope and Application to the Total Synthesis of a Bromopyrrole Alkaloid
  作者：James C. Lanter、Hongfeng Chen、Xuqing Zhang、Zhihua Sui

  DOI：10.1021/ol0525258

  日期：2005.12.1

  [reaction: see text] An asymmetric intermolecular aza variant of the Mannich reaction is reported utilizing chiral sulfinimine anions as the nucleophile and N-sulfonyl aldimines as the electrophilic component. A wide range of nucleophiles and electrophiles are tolerated by the reaction conditions, delivering the condensation products in good to excellent yield with a high degree of stereocontrol. Application

  [反应：见正文]据报道，曼尼希反应的不对称分子间氮杂变体以手性亚磺酰亚胺阴离子为亲核试剂，以N-磺酰基亚胺为亲电组分。反应条件可耐受各种各样的亲核试剂和亲电试剂，以高度立体控制的方式，以高至优异的产率提供缩合产物。报道了这种方法在天然产物的全合成中的应用。
• Asymmetric reduction of racemic 2-isoxazolines
  作者：Masashi Tokizane、Kaori Sato、Tetsuo Ohta、Yoshihiko Ito

  DOI：10.1016/j.tetasy.2008.11.005

  日期：2008.11

  The kinetic resolution of racemic 2-isoxazolines was carried out by asymmetric reduction using borane with 1,2-amino alcohols as a chiral Source. Using excess BH3-THF in the presence of (-)-norephedrine, optically active 1,3-amino alcohol derivatives were obtained with good ee but in lower yield, while the optically active substrates 2-isoxazolines were recovered with modest ee. The asymmetric reduction using 2.0 equiv of BH3-SMe2 was investigated as an alternative strategy for the synthesis of optically active products. After reduction, treatment of the resulting Mixture with Et3N was successful in providing optically active isoxazolidine derivatives in good yields and with good ee. The choice of chiral source was also shown to have a significant effect. In particular, the use of (S)-alpha,alpha-diphenyl-2-pyrrolidinemethanol reversed the enantioselectivity of the recovered Substrates. (C) 2008 Elsevier Ltd. All rights reserved.