3-(Pyridin-2-ylmethylidene)chromen-4-one | 343223-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(Pyridin-2-ylmethylidene)chromen-4-one
• CAS: 343223-20-1
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: DUDLXRUHPVUQFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(Pyridin-2-ylmethylidene)chromen-4-one 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 氢气 、 C₄₆H₆₆FeNO₂P 、 sodium hydroxide 作用下， 以 正己烷 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 反应 12.0h， 以99%的产率得到
  参考文献：
  名称：

  Ir/f-Ampha配合物催化烯酮的不对称顺序氢化：获得具有两个连续手性中心的手性醇的一般途径

  摘要：

  通过使用铱/f-Ampha 配合物作为催化剂，开发了一种通用且高效的 α,β-不饱和酮的不对称顺序氢化方法，以高收率提供具有两个连续立体中心的相应手性醇，并具有优异的非对映和对映选择性（高达 99% 的产率，>20 : 1 dr 和 >99% ee）。对照实验表明，烯酮的 C C 和 C O 键依次氢化，最终的立体选择性由酮的动态动力学拆分决定。此外，DFT 计算表明，外球途径参与了 C C 和 C的减少。O 烯酮键。该方法的合成效用通过克级反应和极低催化剂负载量 (S/C = 20 000) 和获得抗哮喘药物 CP-199,330 的关键手性中间体的简明合成路线得到证明。

  DOI：

  10.1039/d1sc05963g
• 作为产物：
  描述：

  吡啶-2-甲醛 、 2,3-二氢苯并吡喃-4-酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3-(Pyridin-2-ylmethylidene)chromen-4-one
  参考文献：
  名称：

  Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship

  摘要：

  Designed and synthesized were a series of 5H-chromeno[4,3-b]pyridines with substitution at 2- and 4-positions with various 5- or 6-membered heteroaromatics as antitumor agents. They were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Structure activity relationship study showed that 2-furyl or 2-thienyl at 2- or 4-position of central pyridine is crucial in displaying topo I or II inhibitory activity and cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.029

文献信息

• An Asymmetric Hydrogenation/N‐Alkylation Sequence for a Step‐Economical Route to Indolizidines and Quinolizidines
  作者：Wei Zhao、Wenji Wang、Huan Zhou、Qishan Liu、Zhiqing Ma、Haizhou Huang、Mingxin Chang

  DOI：10.1002/anie.202308836

  日期：2023.10.9

  Asymmetric hydrogenation of pyridines and subsequent N-alkylation lead to indolizidines and quinolizidines. The presence of Cl− results in retention of the absolute configuration of the initially formed alcohol. Noncovalent interactions, H-bonding, π-π stacking and electrostatic interactions also play important roles in regulating the stereoselectivity of the reaction process.

  吡啶的不对称氢化和随后的 N-烷基化产生吲哚里西啶和喹里西啶。Cl -的存在导致最初形成的醇的绝对构型得以保留。非共价相互作用、氢键、π-π堆积和静电相互作用在调节反应过程的立体选择性方面也发挥着重要作用。
• Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship
  作者：Uttam Thapa、Pritam Thapa、Radha Karki、Minho Yun、Jae Hun Choi、Yurngdong Jahng、Eunyoung Lee、Kyung-Hwa Jeon、Younghwa Na、Eun-Mi Ha、Won-Jea Cho、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2011.04.029

  日期：2011.8

  Designed and synthesized were a series of 5H-chromeno[4,3-b]pyridines with substitution at 2- and 4-positions with various 5- or 6-membered heteroaromatics as antitumor agents. They were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Structure activity relationship study showed that 2-furyl or 2-thienyl at 2- or 4-position of central pyridine is crucial in displaying topo I or II inhibitory activity and cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.
• 2,4-Diaryl-5H-chromeno [4,3-b]pyridines: Synthesis, Topoisomerase I and II Inhibitory Activity, and Cytotoxicity
  作者：Pritam Thapa、Eung-Seok Lee

  DOI：10.5012/bkcs.2012.33.9.3103

  日期：2012.9.20
• Ir/f-Ampha complex catalyzed asymmetric sequential hydrogenation of enones: a general access to chiral alcohols with two contiguous chiral centers
  作者：Wendian Li、Tilong Yang、Nan Song、Ruihao Li、Jiao Long、Lin He、Xumu Zhang、Hui Lv

  DOI：10.1039/d1sc05963g

  日期：——

  A general and highly efficient method for asymmetric sequential hydrogenation of α,β-unsaturated ketones has been developed by using an iridium/f-Ampha complex as the catalyst, furnishing corresponding chiral alcohols with two contiguous stereocenters in high yields with excellent diastereo- and enantioselectivities (up to 99% yield, >20 : 1 dr and >99% ee). Control experiments indicated that the CC

  通过使用铱/f-Ampha 配合物作为催化剂，开发了一种通用且高效的 α,β-不饱和酮的不对称顺序氢化方法，以高收率提供具有两个连续立体中心的相应手性醇，并具有优异的非对映和对映选择性（高达 99% 的产率，>20 : 1 dr 和 >99% ee）。对照实验表明，烯酮的 C C 和 C O 键依次氢化，最终的立体选择性由酮的动态动力学拆分决定。此外，DFT 计算表明，外球途径参与了 C C 和 C的减少。O 烯酮键。该方法的合成效用通过克级反应和极低催化剂负载量 (S/C = 20 000) 和获得抗哮喘药物 CP-199,330 的关键手性中间体的简明合成路线得到证明。