1-Chloro-2-isothiocyanatomethyl-4-methoxy-5-methoxymethoxy-benzene | 926889-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Chloro-2-isothiocyanatomethyl-4-methoxy-5-methoxymethoxy-benzene
• CAS: 926889-07-8
• 化学式: C₁₁H₁₂ClNO₃S
• 分子量: 273.74
• InChiKey: XENUMJHSBYCPMY-UHFFFAOYSA-N

物化性质

• 沸点：
  386.0±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.05
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-Chloro-2-isothiocyanatomethyl-4-methoxy-5-methoxymethoxy-benzene 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(3-(2-Chloro-4-hydroxy-5-methoxybenzyl)thioureido)-3-(4-tert-butylphenyl)propyl pivalate
  参考文献：
  名称：

  Halogenation of 4-hydroxy-3-methoxybenzyl thiourea TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  Selected potent TRPV1 agonists (1-6) have been modified by 5- or 6-halogenation on the aromatic A-region to analyze their effects on potency and efficacy (agonism versus antagonism). The halogenation caused enhanced functional antagonism at TRPV1 compared to the corresponding prototype agonists. The analysis of SAR indicated that the antagonism was enhanced as the size of the halogen increased (I > Br > CI) and when the 6-position was halogenated. Compounds 23c and 31b were found to be potent full antagonists with K-i (as functional antagonist) = 23.1 and 30.3 nM in rTRPV1/CHO system, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.059
• 作为产物：
  描述：

  3-甲氧基-4-(甲氧基甲氧基)苯甲醛 在 吡啶 、 Oxone 、 lithium hydroxide 、 sodium tetrahydroborate 、 二苯基磷酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 lithium chloride 、 sodium chloride 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 、 甲苯 为溶剂， 生成 1-Chloro-2-isothiocyanatomethyl-4-methoxy-5-methoxymethoxy-benzene
  参考文献：
  名称：

  Halogenation of 4-hydroxy-3-methoxybenzyl thiourea TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  Selected potent TRPV1 agonists (1-6) have been modified by 5- or 6-halogenation on the aromatic A-region to analyze their effects on potency and efficacy (agonism versus antagonism). The halogenation caused enhanced functional antagonism at TRPV1 compared to the corresponding prototype agonists. The analysis of SAR indicated that the antagonism was enhanced as the size of the halogen increased (I > Br > CI) and when the 6-position was halogenated. Compounds 23c and 31b were found to be potent full antagonists with K-i (as functional antagonist) = 23.1 and 30.3 nM in rTRPV1/CHO system, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.059