1-(N-Benzylaminomethyl)-cyclohexanessigsaeure | 146945-12-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(N-Benzylaminomethyl)-cyclohexanessigsaeure
• 英文别名: 2-[1-[(Benzylamino)methyl]cyclohexyl]acetic acid
• CAS: 146945-12-2
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: AWJQZYWPPLZJOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 1-(N-Benzylaminomethyl)-cyclohexanessigsaeure 在 sodium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 5.0h， 以56%的产率得到2-(1-((benzyl(tert-butoxycarbonyl)amino)methyl)cyclohexyl)acetic acid
  参考文献：
  名称：

  Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism

  摘要：

  Six- and seven-membered cyclic enaminones can be prepared using common. environmentally benign reagents. Ammo acids are used as synthetic precursors allowing diversification and the incorporation of chirality The key reaction in this multistep process involves deprotection Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A beta-amino elimination side reaction was identified in a few labile substrates that led to loss of stereochemical purity of degradation. This process can be mitigated in specific cases using mild deprotection conditions NMR and deuteitum-labeling experiments provided valuable insight into the work kings and limitations of this reaction Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond-making and bond-breaking. thus changing die mode of addition to a 6-endo-trig cyclization This method can be used to construct an array of monocyclic and bicyclic scaffolds. many of which me found in well-known natural products (e g indolizidine, quinolizidine, and Stemona alkaloids).

  DOI：

  10.1021/jo100907u
• 作为产物：
  描述：

  苯甲醛 、 加巴喷丁盐酸盐 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 1-(N-Benzylaminomethyl)-cyclohexanessigsaeure
  参考文献：
  名称：

  Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism

  摘要：

  Six- and seven-membered cyclic enaminones can be prepared using common. environmentally benign reagents. Ammo acids are used as synthetic precursors allowing diversification and the incorporation of chirality The key reaction in this multistep process involves deprotection Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A beta-amino elimination side reaction was identified in a few labile substrates that led to loss of stereochemical purity of degradation. This process can be mitigated in specific cases using mild deprotection conditions NMR and deuteitum-labeling experiments provided valuable insight into the work kings and limitations of this reaction Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond-making and bond-breaking. thus changing die mode of addition to a 6-endo-trig cyclization This method can be used to construct an array of monocyclic and bicyclic scaffolds. many of which me found in well-known natural products (e g indolizidine, quinolizidine, and Stemona alkaloids).

  DOI：

  10.1021/jo100907u

文献信息

• BRANCHED CHAIN AMINO ACID-DEPENDENT AMINOTRANSFERASE INHIBITORS AND THEIR USE IN THE TREATMENT OF DIABETIC RETINOPATHY
  申请人：Warner-Lambert Company LLC

  公开号：EP1157000B1

  公开（公告）日：2005-11-02
• [EN] BRANCHED CHAIN AMINO ACID-DEPENDENT AMINOTRANSFERASE INHIBITORS AND THEIR USE IN THE TREATMENT OF DIABETIC RETINOPATHY<br/>[FR] INHIBITEURS D'AMINOTRANSFERASE ACIDES AMINES-DEPENDANTE A CHAINE RAMIFIEE, ET LEUR UTILISATION DANS LE CADRE DU TRAITEMENT DE LA RETINOPATHIE DIABETIQUE
  申请人：WARNER LAMBERT CO

  公开号：WO2001042191A1

  公开（公告）日：2001-06-14

  The present invention is directed to a method for the prophylactic and therapeutic treatment of diabetic retinopathy. The method involves the administration of an inhibitor of formulae (I), (II) and (III) of the branch chain amino acid-dependent aminotransferase (BCAT) pathway to an animal, such as a mammal, in particular a human, in an amount sufficient to treat the retina for diabetic retinopathy prophylactically or therapeutically. The present invention is also directed to several novel inhibitors of formula (IV) of the BCAT pathway. In formulae (I-IV), n, m, X and R1-R13 have the meanings given in the description.
• Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism
  作者：Micah J. Niphakis、Brandon J. Turunen、Gunda I. Georg

  DOI：10.1021/jo100907u

  日期：2010.10.15

  Six- and seven-membered cyclic enaminones can be prepared using common. environmentally benign reagents. Ammo acids are used as synthetic precursors allowing diversification and the incorporation of chirality The key reaction in this multistep process involves deprotection Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A beta-amino elimination side reaction was identified in a few labile substrates that led to loss of stereochemical purity of degradation. This process can be mitigated in specific cases using mild deprotection conditions NMR and deuteitum-labeling experiments provided valuable insight into the work kings and limitations of this reaction Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond-making and bond-breaking. thus changing die mode of addition to a 6-endo-trig cyclization This method can be used to construct an array of monocyclic and bicyclic scaffolds. many of which me found in well-known natural products (e g indolizidine, quinolizidine, and Stemona alkaloids).