(+/-)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile | 198226-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile
• 英文别名: 2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile；(R)-3-chloro-2-cyanophenyl glycidyl ether；2-Chloro-6-[(oxiran-2-yl)methoxy]benzonitrile
• CAS: 198226-62-9
• 化学式: C₁₀H₈ClNO₂
• 分子量: 209.632
• InChiKey: OEZIIOALBOLNJA-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  377.0±22.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile 在 1-丁基-1-甲基吡咯烷六氟磷酸盐 、 Pseudomonas cepacia lipase immobilized on diatomite 、 lithium chloride 、 copper dichloride 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 Acetic acid (S)-2-(3-chloro-2-cyano-phenoxy)-1-chloromethyl-ethyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of calcilytic agent NPS-2143 employing a lipase-mediated resolution protocol

  摘要：

  The kinetic resolution of chlorohydrin (+/-)-6 has been successfully carried out via a lipase-mediated transesterification with vinyl acetate in organic as well as ionic liquid media to yield (R)-alcohol 6 and (S)-acetate 7 in high enantioselectivity. An enantioconvergent synthesis has also been achieved by a Mitsunobu esterification of a mixture of (R)-alcohol 6 and (S)-acetate 7 in one pot to convert the (R)-alcohol 6 to (S)-acetate 7. (S)-Acetate 7 has been hydrolyzed by LiOH center dot H2O to give epoxide (R)-2. This enantiopure epoxide has been used as a chiral precursor for the synthesis of calcilytic agent NPS-2143. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.022
• 作为产物：
  描述：

  3-氯-2-氰基苯基乙酸酯 在 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 25.25h， 生成 (+/-)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile
  参考文献：
  名称：

  Synthesis of the calcilytic ligand NPS 2143

  摘要：

  (R)-3（NPS 2143）是人类钙感受受体（CaSR）的负向变构调节剂，因此代表了一个重要的药理学工具化合物，用于研究CaSR。在此，我们首次披露了对(R)-3的完整实验描述，详细表征和对对映体纯度的评估。我们提出了一种高效、可重复和可扩展的(R)-3合成方法，只需要最少的色谱纯化步骤。通过手性HPLC表明(R)-3的光学纯度非常高（er > 99:1），而且(R)-3的药理学特性完全符合文献报道。

  DOI：

  10.3762/bjoc.9.154

文献信息

• Studies on Agents with Vasodilator and ,B-Blocking Activities. IV.
  作者：Toshimi SEKI、Tomio NAKAO、Takeshi MASUDA、Kohichi HASUMI、Kotaro GOTANDA、Tsutomu ISHIMORI、Seijiro HONMA、Nobuyoshi MINAMI、Kenyu SHIBATA、Kikuo YASUDA

  DOI：10.1248/cpb.44.2061

  日期：——

  A series of novel pyridazinone derivatives (II) having a phenoxypropanolamine moiety was synthesized. Their hypotensive and β-blocking activities were evaluated after intravenous administration of the compounds to anesthetized rats. Among them, the 5-chloro-2-cyanophenoxy derivative (29) showed the promising dual activities and was selected for further studies.

  合成了一系列具有苯氧基丙醇胺结构的新型哒嗪酮衍生物（II）。在静脉注射给麻醉大鼠后，评估了它们的降压和β-阻断活性。其中，5-氯-2-氰基苯氧基衍生物（29）显示出有前途的双重活性，并被选中进行进一步研究。
• Method of using calcilytic compounds
  申请人：NPS Pharmaceuticals, Inc.

  公开号：US06022894A1

  公开（公告）日：2000-02-08

  The present invention features calcilytic compounds. "Calcilytic compounds" refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.

  本发明涉及钙受体拮抗剂化合物。"钙受体拮抗剂化合物"指的是能够抑制钙受体活性的化合物。还描述了利用钙受体拮抗剂化合物来抑制钙受体活性和/或在患者中达到有益效果的方法；以及可用于获取额外钙受体拮抗剂化合物的技术。
• Calcilytic compounds and method of use
  申请人：SmithKline Beecham Corporation

  公开号：US20020052509A1

  公开（公告）日：2002-05-02

  Calcilytic compounds and compositions and their use in treating abnormal bone or mineral homeostasis.

  Calcilytic化合物和组合物及其在治疗异常骨骼或矿物质稳态方面的应用。
• Calcilytic compounds
  申请人：Del Mar G. Eric

  公开号：US20050032850A1

  公开（公告）日：2005-02-10

  The present invention features calcilytic compounds. “Calcilytic compounds” refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.

  本发明涉及钙解离化合物。 "钙解离化合物"是指能够抑制钙受体活性的化合物。还描述了使用钙解离化合物来抑制钙受体活性和/或在患者中获得有益效果的方法；以及可用于获得其他钙解离化合物的技术。
• CALCILYTIC COMPOUNDS
  申请人：Del Mar Eric G.

  公开号：US20070249702A1

  公开（公告）日：2007-10-25

  The present invention features calcilytic compounds. “Calcilytic compounds” refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.

  本发明涉及钙解离化合物。 “钙解离化合物”是指能够抑制钙受体活性的化合物。同时，本发明还描述了使用钙解离化合物来抑制钙受体活性和/或在患者中获得有益效果的方法；以及可用于获得其他钙解离化合物的技术。