methyl 4-oxo-4-phenyl-2,3-cyclopropanobutanoate | 6366-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-oxo-4-phenyl-2,3-cyclopropanobutanoate
• 英文别名: trans-methyl 2-benzoylcylopropane-1carboxylate；trans-2-Benzoyl-cyclopropancarbonsaeure-methylester；trans-2-Benzoylcyclopropancarbonsaeuremethylester；methyl (1S,2S)-2-benzoylcyclopropane-1-carboxylate
• CAS: 6366-30-9；6421-94-9；91963-15-4
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: YMOOOSOZVWJGNV-UWVGGRQHSA-N

物化性质

• 沸点：
  301.4±35.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-oxo-4-phenyl-2,3-cyclopropanobutanoate 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 8.0h， 以65%的产率得到methyl 4-hydroxy-4-phenyl-2,3-cyclopropanobutanoate
  参考文献：
  名称：

  Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride

  摘要：

  4-芳基-4-氧代酯在室温下与甲醇中的NaBH₄发生反应，可以轻易地同时还原其酮基和酯基，生成相应的1-芳基-1,4-丁二醇，而4-烷基-4-氧代酯则通过选择性地还原酮基部分，得到相应的1,4-丁内酯。本文详细描述了这一反应的全面和系统性的研究结果。

  DOI：

  10.3762/bjoc.6.94
• 作为产物：
  描述：

  Methyl 2-methyl-3-methylsulfonyloxy-4-oxo-4-phenylbutanoate 在 N-甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到methyl 4-oxo-4-phenyl-2,3-cyclopropanobutanoate
  参考文献：
  名称：

  A New Photochemical Route to Cyclopropanes

  摘要：

  DOI：

  10.1002/1521-3773(20010316)40:6<1064::aid-anie10640>3.0.co;2-5

文献信息

• Photochemical Synthesis of Highly Functionalized Cyclopropyl Ketones
  作者：Pablo Wessig、Olaf Mühling

  DOI：10.1002/hlca.200390086

  日期：2003.3

  trisubstituted cyclopropyl ketones 11 were prepared by irradiation of ketones 3 and 5, which bear a leaving group adjacent to the carbonyl C-atom. The required ketones 3 could be easily synthesized either by functionalization of ketones 1 with a hypervalent iodine reagent, 2, or by O-sulfonylation of α-hydroxy ketones 7. The nitrates 5 were obtained by treatment of the corresponding α-bromo ketones with AgNO3

  通过辐射酮3和5制备一系列二和三取代的环丙基酮11，所述酮3和5带有与羰基C-原子相邻的离去基团。所需的酮3可以通过使用高价碘试剂2对酮1进行功能化或通过α-羟基酮7的O-磺酰化来轻松合成。通过用AgNO 3处理相应的α-溴代酮获得硝酸盐5。3和5的照射必须在除酸剂（1-甲基-1 H-咪唑）的存在下进行，以获得高收率的环丙烷11。除其他事项外，该方法的合成效率通过制备高收率的高应变双环[2.1.0]戊烷11i得以证明。通过光动力学测量以及量子化学计算研究了光化学环化的机理。已经表明，离去基团的存在实质上影响了光化学反应级联的所有步骤。还确定了11j和exo - 11k的X射线晶体结构。
• Preparation of Aryl‐Substituted<i>E</i>‐Homoallylic Bromides from Cyclopropylcarbinol and PBr₃
  作者：Sanchita Roy、Sharmistha Guha、Samit Kumar Dutta、Sanjay Bhar

  DOI：10.1080/00397910600602768

  日期：2006.7

  Abstract An expeditious synthesis of aryl substituted E‐homoallylic bromides has been accomplished by the cleavage of cyclopropylcarbinols with phosphorus tribromide.

  摘要 通过用三溴化磷裂解环丙基甲醇，实现了芳基取代的 E-高烯丙基溴化物的快速合成。
• Chiral cyclopentadienyl Rh^III-catalyzed enantioselective cyclopropanation of electron-deficient olefins enable rapid access to UPF-648 and oxylipin natural products
  作者：Coralie Duchemin、Nicolai Cramer

  DOI：10.1039/c8sc05702h

  日期：——

  Chiral cyclopentadienyl RhIII complexes efficiently catalyze enantioselective cyclopropanations of electron-deficient olefins with N-enoxysuccinimides as the C1 unit. Excellent asymmetric inductions and high diastereoselectivities can be obtained for a wide range of substrate combinations. The reaction proceeds under mild conditions without precautions to exclude air and water. Moreover, the synthetic

  手性环戊二烯基 Rh III配合物可有效催化以N-烯氧基琥珀酰亚胺为 C1 单元的缺电子烯烃的对映选择性环丙烷化反应。对于广泛的底物组合可以获得优异的不对称诱导和高非对映选择性。反应在温和条件下进行，无需采取排除空气和水的措施。此外，通过氧脂素天然产物家族成员和 KMO 抑制剂 UPF-648 的简明合成，证明了所开发方法的合成实用性。
• KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
  申请人：CHDI FOUNDATION, INC.

  公开号：US20150057238A1

  公开（公告）日：2015-02-26

  Certain compounds, or pharmaceutically acceptable salts or prodrugs thereof, are provided herein. Also provided are pharmaceutical compositions comprising at least one compound, or pharmaceutically acceptable salt or prodrug thereof, described herein and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of KMO activity are described, which comprise administering to such patients an amount of at least one compound, or pharmaceutically acceptable salt or prodrug thereof, described herein effective to reduce signs or symptoms of the disease or disorder are disclosed. These diseases include neurodegenerative disorders such as Huntington's disease. Also described are methods of treatment include administering at least one compound, or pharmaceutically acceptable salt or prodrug thereof, described herein as a single active agent or administering at least one compound, or pharmaceutically acceptable salt or prodrug thereof, described herein in combination with one or more other therapeutic agents. Also provided are methods for screening compounds capable of inhibiting KMO activity.

  本文提供了某些化合物，或其药学上可接受的盐或前药。还提供了包含至少一种化合物或其药学上可接受的盐或前药及一种或多种药学上可接受的载体的制药组合物。本文描述了治疗对KMO活性抑制有反应的某些疾病和障碍的患者的方法，包括向这些患者施用至少一种本文所述的化合物或其药学上可接受的盐或前药的有效量，以减少疾病或障碍的症状。这些疾病包括神经退行性疾病，如亨廷顿病。本文还描述了治疗方法，包括将至少一种本文所述的化合物或其药学上可接受的盐或前药作为单一活性剂施用，或将至少一种本文所述的化合物或其药学上可接受的盐或前药与一种或多种其他治疗剂联合施用。还提供了筛选能够抑制KMO活性的化合物的方法。
• Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof
  申请人：CHDI Foundation, Inc.

  公开号：US10442782B2

  公开（公告）日：2019-10-15

  Certain compounds, or pharmaceutically acceptable salts or prodrugs thereof, are provided herein. Also provided are pharmaceutical compositions comprising at least one compound, or pharmaceutically acceptable salt or prodrug thereof, described herein and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of KMO activity are described, which comprise administering to such patients an amount of at least one compound, or pharmaceutically acceptable salt or prodrug thereof, described herein effective to reduce signs or symptoms of the disease or disorder are disclosed. These diseases include neurodegenerative disorders such as Huntington's disease. Also described are methods of treatment include administering at least one compound, or pharmaceutically acceptable salt or prodrug thereof, described herein as a single active agent or administering at least one compound, or pharmaceutically acceptable salt or prodrug thereof, described herein in combination with one or more other therapeutic agents. Also provided are methods for screening compounds capable of inhibiting KMO activity.

  本文提供了某些化合物或其药学上可接受的盐或原药。还提供了包含至少一种本文所述化合物或其药学上可接受的盐或原药以及一种或多种药学上可接受的载体的药物组合物。描述了治疗对抑制 KMO 活性有反应的某些疾病和失调患者的方法，其中包括向此类患者施用一定量的本文所述的至少一种化合物或其药学上可接受的盐或原药，以有效减少疾病或失调的体征或症状。这些疾病包括神经退行性疾病，如亨廷顿氏病。还描述了治疗方法，包括将本文所述的至少一种化合物或其药学上可接受的盐或原药作为单一活性剂给药，或将本文所述的至少一种化合物或其药学上可接受的盐或原药与一种或多种其它治疗剂联合给药。还提供了筛选能够抑制 KMO 活性的化合物的方法。