(S)-2-phenyl-decylamine | 167422-39-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-phenyl-decylamine
• 英文别名: (2S)-2-phenyldecan-1-amine
• CAS: 167422-39-1
• 化学式: C₁₆H₂₇N
• 分子量: 233.397
• InChiKey: JVYWECIBYBFYMJ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  17.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (S)-2-phenyl-decylamine 在 4-二甲氨基吡啶 作用下， 以 氘代氯仿 为溶剂， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-N-((S)-2-phenyl-decyl)-propionamide
  参考文献：
  名称：

  的非还原对映体选择性开环ñ -二异丙与α，α，α'，α'-四芳基-1,3-二氧戊环-4,5- dimethanolate（甲基磺酰基）二甲

  摘要：

  二环丙氧基钛TADDOLate将双环和三环内消旋-N-（甲基磺酰基）二甲酰亚胺1a-f对映体转化为异丙基[（磺酰胺基）羰基]-羧酸盐2a-f（产率为75-92％；参见方案3）。产物的对映体比例在86:14至97：3之间，并且从CH 2 Cl 2 /己烷中重结晶得到对映体纯的磺酰胺基酯2（方案3）。对映选择性与所用TADDOL的对映体过量显示线性关系（图3）。还原酯基和羧酰胺基（LiAlH 4）和酰亚胺开环的产物2中磺酰胺基（Red-Al）的额外还原裂解分别得到羟基磺酰胺3和氨基醇4（流程4）。磺酰胺基酯2的绝对构型是通过化学相关性（与2a，b；方案6），对3e的樟脑酸酯的X射线分析（图1）以及对羟基苯甲酸酯的19 F-NMR分析确定的羟基磺酰胺3的较硬酯（表1）。对于伯醇和胺的的绝对构型的分配的一般建议式HXCH 2 CHR 1 - [R 2，X = O，NH，建议（见11在表1中）。从2

  DOI：

  10.1002/hlca.19960790328
• 作为产物：
  描述：

  反式硝基苯乙烯 、 dioctylzinc 在 Raney-Ni W₂ (R,R)-tetraphenyl Ti-TADDOLate 、 氢气 作用下， 生成 (R)-2-phenyl-decylamine 、 (S)-2-phenyl-decylamine
  参考文献：
  名称：

  Enantioselective conjugate addition of primary dialkylzinc reagents to 2-aryl- and 2-heteroaryl-nitroolefins mediated by titanium-TADDOLates preparation of enantioenriched 2-aryl-alkylamines

  摘要：

  The addition of dialkylzinc to nitroolefins is catalyzed by Lewis acids such as MgBr2, MgI2, and chlorotitanates. Using the (R,R)-Ti-TADDOLates the addition of diethyl-, dibutyl-, and dioctyl zinc to 2-aryl-nitroethenes is shown to be enantioselective with yields near 90% and enantiomer ratios of ca. 9:1 (products 3-12; enantiomer enrichment by crystallization is possible in some cases). Reduction of the 2-aryl-nitroalkanes thus obtained by catalytic hydrogenation over Pd/C or Raney-Ni leads to the corresponding enantioenriched 2-aryl-alkylamines (products 13-21). The enantiopurity of the nitroalkanes and amines was determined by chromatography on chiral columns. The configuration of the products is assigned (S) by optical comparison and by analogy (comparison of five different types of physical data). The relative topicity of the process is unlike (ul = R,R/Si or S,S/Re).

  DOI：

  10.1016/0040-4020(94)01100-e

文献信息

• Enantioselective conjugate addition of primary dialkylzinc reagents to 2-aryl- and 2-heteroaryl-nitroolefins mediated by titanium-TADDOLates preparation of enantioenriched 2-aryl-alkylamines
  作者：Harald Schäfer、Dieter Seebach

  DOI：10.1016/0040-4020(94)01100-e

  日期：1995.2

  The addition of dialkylzinc to nitroolefins is catalyzed by Lewis acids such as MgBr2, MgI2, and chlorotitanates. Using the (R,R)-Ti-TADDOLates the addition of diethyl-, dibutyl-, and dioctyl zinc to 2-aryl-nitroethenes is shown to be enantioselective with yields near 90% and enantiomer ratios of ca. 9:1 (products 3-12; enantiomer enrichment by crystallization is possible in some cases). Reduction of the 2-aryl-nitroalkanes thus obtained by catalytic hydrogenation over Pd/C or Raney-Ni leads to the corresponding enantioenriched 2-aryl-alkylamines (products 13-21). The enantiopurity of the nitroalkanes and amines was determined by chromatography on chiral columns. The configuration of the products is assigned (S) by optical comparison and by analogy (comparison of five different types of physical data). The relative topicity of the process is unlike (ul = R,R/Si or S,S/Re).
• Nonreductive Enantioselective Ring Opening of<i>N</i>-(Methylsulfonyl)dicarboximides with Diisopropoxytitanium α,α,α′,α′-Tetraaryl-1,3-dioxolane-4,5-dimethanolate
  作者：Diego J. Ramón、Gabriela Guillena、Dieter Seebach

  DOI：10.1002/hlca.19960790328

  日期：1996.5.8

  dicarboximides 1a–f are converted enantioselectively to isopropyl [(sulfonamido)carbonyl]-carboxylates 2a–f by diisopropoxytitanium TADDOLate (75–92% yield; see Scheme 3). The enantiomer ratios of the products are between 86:14 and 97:3, and recrystallization from CH2Cl2/hexane leads to enantiomerically pure sulfonamido esters 2 (Scheme 3). The enantioselectivity shows a linear relationship with the

  二环丙氧基钛TADDOLate将双环和三环内消旋-N-（甲基磺酰基）二甲酰亚胺1a-f对映体转化为异丙基[（磺酰胺基）羰基]-羧酸盐2a-f（产率为75-92％；参见方案3）。产物的对映体比例在86:14至97：3之间，并且从CH 2 Cl 2 /己烷中重结晶得到对映体纯的磺酰胺基酯2（方案3）。对映选择性与所用TADDOL的对映体过量显示线性关系（图3）。还原酯基和羧酰胺基（LiAlH 4）和酰亚胺开环的产物2中磺酰胺基（Red-Al）的额外还原裂解分别得到羟基磺酰胺3和氨基醇4（流程4）。磺酰胺基酯2的绝对构型是通过化学相关性（与2a，b；方案6），对3e的樟脑酸酯的X射线分析（图1）以及对羟基苯甲酸酯的19 F-NMR分析确定的羟基磺酰胺3的较硬酯（表1）。对于伯醇和胺的的绝对构型的分配的一般建议式HXCH 2 CHR 1 - [R 2，X = O，NH，建议（见11在表1中）。从2