3-(pyridin-3-yl)cyclopent-2-en-1-one | 1107641-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(pyridin-3-yl)cyclopent-2-en-1-one
• 英文别名: 3-(pyridin-3-yl)-cyclopent-2-enone；3-(Pyridin-3-yl)cyclopent-2-enone；3-pyridin-3-ylcyclopent-2-en-1-one
• CAS: 1107641-04-2
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: YAVOAPLWNIVMIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴吡啶 、 2-环戊烯酮 在 potassium fluoride 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以68%的产率得到3-(pyridin-3-yl)cyclopent-2-en-1-one
  参考文献：
  名称：

  Selective Heck reaction of aryl bromides with cyclopent-2-en-1-one or cyclohex-2-en-1-one

  摘要：

  The selective Heck reaction of cyclopent-2-en-1-one or cyclohex-2-en-1-one with aryl bromides gives a simple access to the corresponding 3-arylcycloalk-2-en-1-ones. The choice of the base was found to be crucial to avoid the formation of 3-arylcyclopentanones or 3-arylcyclohexanones as side-products. Using KF as base, DMF as solvent and Pd(OAc)(2) as catalyst, the target products were obtained in moderate to good yields with a variety of aryl bromides. Substituents such as fluoro, trifluoromethyl, acetyl, benzoyl, formyl, ester or nitrile on the aryl bromide are tolerated. Sterically congested aryl bromides or bromopyridines can also be employed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.006

文献信息

• [EN] NOVEL CYP17 INHIBITORS/ANTIANDROGENS<br/>[FR] NOUVEAUX INHIBITEURS DE CYP17/ANTIANDROGÈNES
  申请人：ORION CORP

  公开号：WO2014202827A1

  公开（公告）日：2014-12-24

  Compounds of formula (I), wherein R1 to R8 A, B, Z1 and Z2 are as defined in the claims and pharmaceutically acceptable salts and esters thereof are disclosed. The compounds of formula (I) possess utility as androgen receptor antagonists (inhibitors) and/or cytochrome P450 monooxygenase 17a-hydroxylase/17,20-lyase (CYP17) inhibitors. The compounds are useful as medicaments in the treatment of cancer, particularly prostate cancer, and other androgen dependent conditions and diseases where androgen antagonism is desired.

  公式（I）的化合物，其中R1至R8，A，B，Z1和Z2如权利要求中所定义，并且其药用盐和酯被披露。公式（I）的化合物具有作为雄激素受体拮抗剂（抑制剂）和/或细胞色素P450单加氧酶17a-羟化酶/17,20-裂解酶（CYP17）抑制剂的效用。这些化合物在治疗癌症，特别是前列腺癌，以及其他需要雄激素拮抗作用的疾病和情况中作为药物是有用的。
• NOVEL CYP17 INHIBITORS/ANTIANDROGENS
  申请人：ORION CORPORATION

  公开号：US20160130254A1

  公开（公告）日：2016-05-12

  Compounds of formula (I) wherein R 1 to R 8 , A, B, Z 1 , and Z 2 are as defined in the claims and pharmaceutically acceptable salts and esters thereof are disclosed. The compounds of formula (I) possess utility as androgen receptor antagonists (inhibitors) and/or cytochrome P450 monooxygenase 17α-hydroxylase/17,20-lyase (CYP17) inhibitors. The compounds are useful as medicaments in the treatment of cancer, particularly prostate cancer, and other androgen dependent conditions and diseases where androgen antagonism is desired.

  公式（I）化合物的结构式中，其中R1至R8，A，B，Z1和Z2如权利要求所定义，并且其药学上可接受的盐和酯被揭示。公式（I）化合物具有作为雄激素受体拮抗剂（抑制剂）和/或细胞色素P450单加氧酶17α-羟化酶/17,20-裂解酶（CYP17）抑制剂的效用。这些化合物在治疗癌症，特别是前列腺癌和其他需要雄激素拮抗剂的疾病和病情中作为药物是有用的。
• US9890139B2
  申请人：——

  公开号：US9890139B2

  公开（公告）日：2018-02-13
• Selective Heck reaction of aryl bromides with cyclopent-2-en-1-one or cyclohex-2-en-1-one
  作者：Yacoub Fall、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.tet.2008.11.006

  日期：2009.1

  The selective Heck reaction of cyclopent-2-en-1-one or cyclohex-2-en-1-one with aryl bromides gives a simple access to the corresponding 3-arylcycloalk-2-en-1-ones. The choice of the base was found to be crucial to avoid the formation of 3-arylcyclopentanones or 3-arylcyclohexanones as side-products. Using KF as base, DMF as solvent and Pd(OAc)(2) as catalyst, the target products were obtained in moderate to good yields with a variety of aryl bromides. Substituents such as fluoro, trifluoromethyl, acetyl, benzoyl, formyl, ester or nitrile on the aryl bromide are tolerated. Sterically congested aryl bromides or bromopyridines can also be employed. (C) 2008 Elsevier Ltd. All rights reserved.