m-Tolylamino-acetic acid tert-butyl ester | 160801-46-7

• 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: m-Tolylamino-acetic acid tert-butyl ester
• 英文别名: Tert-butyl 2-(3-methylanilino)acetate
• CAS: 160801-46-7
• 化学式: C₁₃H₁₉NO₂
• mdl: MFCD12148614
• 分子量: 221.299
• InChiKey: DSFHUXZUNQOMPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  m-Tolylamino-acetic acid tert-butyl ester 在 碘代三甲硅烷 、 水 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.92h， 生成 [(3-Acetylsulfanyl-2-methyl-propionyl)-m-tolyl-amino]-acetic acid
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives

  摘要：

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00379a013
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 3-甲基苯胺 在 sodium acetate 作用下， 以 乙醇 为溶剂， 生成 m-Tolylamino-acetic acid tert-butyl ester
  参考文献：
  名称：

  可见光促进 N-苯基 α-氨基酸 α-苄基化为 α-氨基苯丙素

  摘要：

  通过在温和条件下将容易获得的N-苯基甘氨酸酯与草酸苄酯作为偶联伙伴进行α-CH苄基化，开发了一种在蓝色发光二极管照射下合成α-氨基苯丙素的新方法。一系列N-苯基甘氨酸酯已成功转化为 α-氨基苯丙素产品，收率中等至良好。该方法的实用性通过其在天然产物后期修饰中的应用而得到强调。

  DOI：

  10.1021/acs.joc.3c01196

文献信息

• N-ACYL ANTHRANILIC ACID DERIVATIVE OR SALT THEREOF
  申请人：Yokotani Junichi

  公开号：US20110275797A1

  公开（公告）日：2011-11-10

  An N-acyl anthranilic acid derivative represented by general formula (1) or a salt thereof is useful for prevention or treatment of diseases associated with excessive production of collagen. (In the formula, R 1 represents a carboxyl group or the like; R 2 represents a hydrogen atom or the like; R 3 represents an optionally substituted aryl group or the like; X 1 represents a carbonyl group; X 2 represents a bonding hand; X 3 represents a bonding hand; X 4 represents a bonding hand or the like; and A represents an optionally substituted phenyl group or the like.)

  通用公式（1）表示的N-酰基蒽酸衍生物或其盐对预防或治疗与胶原蛋白过度产生相关的疾病具有用处。（在该公式中，R1代表羧基或类似物；R2代表氢原子或类似物；R3代表可选择取代的芳基或类似物；X1代表羰基；X2代表连接手；X3代表连接手；X4代表连接手或类似物；A代表可选择取代的苯基或类似物。）
• [EN] N-ACYL ANTHRANILIC ACID DERIVATIVE OR SALT THEREOF<br/>[FR] DÉRIVÉ DE L'ACIDE N-ACYLE ANTHRANILIQUE OU SON SEL
  申请人：TOYAMA CHEMICAL CO LTD

  公开号：WO2010087430A1

  公开（公告）日：2010-08-05

  一般式「式中、Ｒ１は、カルボキシル基などを；Ｒ２は、水素原子などを；Ｒ３は、置換されていてもよいアリール基などを；Ｘ１は、カルボニル基を；Ｘ２は、結合手を；Ｘ３は、結合手を；Ｘ４は、結合手などを；Ａは、置換されていてもよいフェニル基などを示す。」で表されるＮ－アシルアントラニル酸誘導体またはその塩は、コラーゲンの過剰産生が関与する疾患の予防または治療などの処置に有用である。
• Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives
  作者：John T. Suh、Jerry W. Skiles、Bruce E. Williams、Raymond D. Youssefyeh、Howard Jones、Bernard Loev、Edward S. Neiss、Alfred Schwab、William S. Mann

  DOI：10.1021/jm00379a013

  日期：1985.1

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.
• Visible-Light-Promoted α-Benzylation of N-Phenyl α-Amino Acids to α-Amino Phenylpropanoids
  作者：Lin Wang、Kang Li、Tian Ye、Lei Huang、Huilan Wu、Jingxuan Zhang、Hongqi Xie、Yisong Liu、Jianguo Zeng、Pi Cheng

  DOI：10.1021/acs.joc.3c01196

  日期：2023.8.18

  A new method for the synthesis of α-amino phenylpropanoids under blue light-emitting diode irradiation has been developed through α-C-H benzylation of readily available N-phenyl glycine ester with benzyl oxalates as a coupling partner under mild conditions. A range of N-phenyl glycine esters were successfully converted to α-amino phenylpropanoid products in moderate to good yields. The utility of this

  通过在温和条件下将容易获得的N-苯基甘氨酸酯与草酸苄酯作为偶联伙伴进行α-CH苄基化，开发了一种在蓝色发光二极管照射下合成α-氨基苯丙素的新方法。一系列N-苯基甘氨酸酯已成功转化为 α-氨基苯丙素产品，收率中等至良好。该方法的实用性通过其在天然产物后期修饰中的应用而得到强调。