Benzoesaeure-(cis-2-methylcyclohexylamid) | 836-05-5

• 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: Benzoesaeure-(cis-2-methylcyclohexylamid)
• 英文别名: cis-2-Benzamido-1-methyl-cyclohexan；(+/-)-N-(cis-2-methyl-cyclohexyl)-benzamide；(+/-)-N-(cis-2-Methyl-cyclohexyl)-benzamid；(+/-)-cis-2-Benzamino-1-methyl-cyclohexan；N-[(1S,2R)-2-methylcyclohexyl]benzamide
• CAS: 836-05-5；29569-78-6；43226-07-9；92499-44-0
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: BDVZXZBKLDUQNY-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Benzoesaeure-(cis-2-methylcyclohexylamid) 在 盐酸 作用下， 反应 96.0h， 生成 (1S,2R)-2-甲基环己胺
  参考文献：
  名称：

  Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

  摘要：

  The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10294-0
• 作为产物：
  描述：

  (-)-顺式-2-苄胺基环己基羧酸 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 13.0h， 生成 Benzoesaeure-(cis-2-methylcyclohexylamid)
  参考文献：
  名称：

  Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

  摘要：

  The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10294-0

文献信息

• Stereoretentive Copper(II)-Catalyzed Ritter Reactions of Secondary Cycloalkanols
  作者：Mohammed H. Al-huniti、Salvatore D. Lepore

  DOI：10.1002/adsc.201300233

  日期：2013.10.11

  A Ritter-like coupling reaction of cyclic alcohols and both aryl and alkyl nitriles to form amides catalyzed by copper (II) triflate is described. These reactions proceed in good yields under mild and often solvent-free conditions. With 2- and 3-substituted cycloalkanols, amide products are formed with near complete retention of configuration. This is likely due to fast nucleophilic capture of a non-planar

  描述了环状醇与芳基和烷基腈两者的Ritter-like偶联反应，形成了由三氟甲磺酸铜（II）催化形成的酰胺。这些反应在温和且通常无溶剂的条件下以高收率进行。与2-和3-取代的环烷醇一起，形成酰胺产物，几乎完全保留了构型。这可能是由于通过环超共轭稳定的非平面碳正离子（超高聚物）的快速亲核捕获。该新颖的催化循环的关键方面是亚硫酰氯原位活化醇底物以形成亚氯硫酸盐。
• 金属络合物、制备方法和应用及其中间体
  申请人：中国科学院上海有机化学研究所

  公开号：CN107445999B

  公开（公告）日：2020-11-13

  本发明公开了一种金属络合物、制备方法和应用及其中间体。本发明通过将一种手性双膦配体或者其金属络合物作为催化剂用于纯烷基类四取代环状烯酰胺的不对称氢化反应，实现了对手性环状胺类化合物的合成，该手性双膦配体或其金属络合物在该不对称氢化反应中催化效率高，产物手性纯度好，底物适应范围大。
• Skita; Berendt, Chemische Berichte, 1919, vol. 52, p. 1526
  作者：Skita、Berendt

  DOI：——

  日期：——
• Gutt, Chemische Berichte, 1907, vol. 40, p. 2066
  作者：Gutt

  DOI：——

  日期：——
• Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation
  作者：Tadashi Eguchi、Miki Fukuda、Yumiko Toyooka、Katsumi Kakinuma

  DOI：10.1016/s0040-4020(97)10294-0

  日期：1998.1

  The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.