1-(4-methoxyphenyl)-3-(3-(dimethylamino)propyl)carbodiimide

• 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: 1-(4-methoxyphenyl)-3-(3-(dimethylamino)propyl)carbodiimide
• 化学式: C₁₃H₁₉N₃O
• 分子量: 233.313
• InChiKey: CTYTUXFGVFEKMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲磺酸甲酯 、 1-(4-methoxyphenyl)-3-(3-(dimethylamino)propyl)carbodiimide 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Substituent effects in the addition of carboxylic acids to arylcarbodiimidesElectronic supplementary information (ESI) available: details on the preparation of substrates and carbodiimide characterization data. See http://www.rsc.org/suppdata/p2/b1/b105867n/

  摘要：

  在水溶液中，RCOOH（R = CH3–, CH3OCH2–, ClCH2–, Cl2CH–）与ArNCNCH2CH2CH2N+(CH3)3 [Ar = C6H5–, 3-ClC6H4–, 4-CH3OC6H4–, 3,4-Cl2C6H3–, 2,4-(CH3O)2C6H3–]反应生成瞬态O-酰基异脲的加成速率，已通过测量pH值的变化来进行评估。相对活性表明反应机制涉及羧酸盐阴离子与少量存在的一或二质子化芳基碳二亚胺的加成。注意到反应速率与羧酸盐亲核试剂的碱性之间仅存在微弱依赖关系（Brønsted β值约为0.2）。芳基连接氮原子的初步质子化容易性（根据相应取代喹啉的碱度估算）似乎主导了反应活性，因此，芳环取代基的电子供体性质使得这种芳基碳二亚胺对羧酸盐的加成更为敏感。

  DOI：

  10.1039/b105867n
• 作为产物：
  描述：

  1-(3-Dimethylamino-propyl)-3-(4-methoxy-phenyl)-urea 在 苄基三乙基溴化铵 、 potassium carbonate 、 对甲苯磺酰氯 作用下， 以 苯 为溶剂， 生成 1-(4-methoxyphenyl)-3-(3-(dimethylamino)propyl)carbodiimide
  参考文献：
  名称：

  Substituent effects in the addition of carboxylic acids to arylcarbodiimidesElectronic supplementary information (ESI) available: details on the preparation of substrates and carbodiimide characterization data. See http://www.rsc.org/suppdata/p2/b1/b105867n/

  摘要：

  在水溶液中，RCOOH（R = CH3–, CH3OCH2–, ClCH2–, Cl2CH–）与ArNCNCH2CH2CH2N+(CH3)3 [Ar = C6H5–, 3-ClC6H4–, 4-CH3OC6H4–, 3,4-Cl2C6H3–, 2,4-(CH3O)2C6H3–]反应生成瞬态O-酰基异脲的加成速率，已通过测量pH值的变化来进行评估。相对活性表明反应机制涉及羧酸盐阴离子与少量存在的一或二质子化芳基碳二亚胺的加成。注意到反应速率与羧酸盐亲核试剂的碱性之间仅存在微弱依赖关系（Brønsted β值约为0.2）。芳基连接氮原子的初步质子化容易性（根据相应取代喹啉的碱度估算）似乎主导了反应活性，因此，芳环取代基的电子供体性质使得这种芳基碳二亚胺对羧酸盐的加成更为敏感。

  DOI：

  10.1039/b105867n

文献信息

• Synthesis of Highly Basic Hexasubstituted Biguanides by Environmentally Friendly Methods
  作者：Davor Margetić、Mirjana Eckert-Maksić、Zoran Glasovac、Pavle Trošelj、Iva Jušinski

  DOI：10.1055/s-0033-1339876

  日期：——

  A series of hexasubstituted biguanides was synthetized employing nonconventional and environmentally friendly methods. Their properties were studied computationally (basicity) and experimentally (basicity and catalytic properties in transesterification reaction).
• Substituent effects in the addition of carboxylic acids to arylcarbodiimidesElectronic supplementary information (ESI) available: details on the preparation of substrates and carbodiimide characterization data. See http://www.rsc.org/suppdata/p2/b1/b105867n/
  作者：William L. Mock、Krzysztof J. Ochwat

  DOI：10.1039/b105867n

  日期：2002.3.25

  Rates of addition in aqueous solution of RCOOH (R = CH3–, CH3OCH2–, ClCH2–, Cl2CH–) to ArNCNCH2CH2CH2N+(CH3)3 [Ar = C6H5–, 3-ClC6H4–, 4-CH3OC6H4–, 3,4-Cl2C6H3–, 2,4-(CH3O)2C6H3–] yielding a transient O-acylisourea, have been measured as a function of pH. Relative activities indicate a reaction mechanism in which a carboxylate anion adds to a mono- or di-protonated arylcarbodiimide, available in minor amounts. Only a weak dependence of reaction velocity upon basicity of carboxylate nucleophile is noted (Brønsted β value of ∼0.2). Ease of prefatory protonation of aryl-attached nitrogen within ArNCNR′ (as estimated from the basicity of correspondingly substituted quinolines) appears to dominate reactivity, so that the presence of electron-donating ring substituents renders such an arylcarbodiimide significantly more susceptible to addition by carboxylates.

  在水溶液中，RCOOH（R = CH3–, CH3OCH2–, ClCH2–, Cl2CH–）与ArNCNCH2CH2CH2N+(CH3)3 [Ar = C6H5–, 3-ClC6H4–, 4-CH3OC6H4–, 3,4-Cl2C6H3–, 2,4-(CH3O)2C6H3–]反应生成瞬态O-酰基异脲的加成速率，已通过测量pH值的变化来进行评估。相对活性表明反应机制涉及羧酸盐阴离子与少量存在的一或二质子化芳基碳二亚胺的加成。注意到反应速率与羧酸盐亲核试剂的碱性之间仅存在微弱依赖关系（Brønsted β值约为0.2）。芳基连接氮原子的初步质子化容易性（根据相应取代喹啉的碱度估算）似乎主导了反应活性，因此，芳环取代基的电子供体性质使得这种芳基碳二亚胺对羧酸盐的加成更为敏感。