1-(4-chlorophenyl)-4-methyl-1-penten-3-one | 1577-33-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(4-chlorophenyl)-4-methyl-1-penten-3-one
• 英文别名: 1-(4-Chlor-phenyl)-4-methyl-pent-1-en-3-on；1-(4-chlorophenyl)-4-methylpent-1-en-3-one
• CAS: 1577-33-9
• 化学式: C₁₂H₁₃ClO
• 分子量: 208.688
• InChiKey: JDMLNXSURTZNJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-4-methyl-1-penten-3-one 在 N-[（1R，2R）-2-氨基环己基]-N''-[[（（1R，4aS，10aR）-1,2,3,4,4a，9,10,10a-八氢-1,4a-二甲基-7-异丙基-1-菲基]甲基]硫脲 、 溶剂黄146 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 168.0h， 生成 isopropyl (3R)-3-(4-chlorophenyl)-4-nitrobutanoate
  参考文献：
  名称：

  硝基烷对烯的高对映选择性迈克尔加成反应及其在（R）-巴氯芬和（R）-苯酚丁醚的合成中的应用

  摘要：

  摘要 开发了对α，β-不饱和酮的硝基烷烃的高对映选择性迈克尔加成反应。在基于脱氢松香胺的手性伯胺-硫脲催化剂的存在下，可获得具有出色的对映选择性（高达99％ee）和高达96％收率的γ-硝基酮。该方案已成功用于（R）-baclofen和（R）-pheni的不对称合成中，但收率高且对映选择性优异。 开发了对α，β-不饱和酮的硝基烷烃的高对映选择性迈克尔加成反应。在基于脱氢松香胺的手性伯胺-硫脲催化剂的存在下，可获得具有出色的对映选择性（高达99％ee）和高达96％收率的γ-硝基酮。该方案已成功用于（R）-baclofen和（R）-pheni的不对称合成中，但收率高且对映选择性优异。

  DOI：

  10.1055/s-0034-1380203
• 作为产物：
  描述：

  1-溴-3-甲基-2-丁酮 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.0h， 生成 1-(4-chlorophenyl)-4-methyl-1-penten-3-one
  参考文献：
  名称：

  Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

  摘要：

  An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6 pi-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

  DOI：

  10.1021/acs.orglett.5b02903

文献信息

• Evaluation of some Mannich bases of conjugated styryl ketones and related compounds versus the WiDr colon cancer in vitro
  作者：Jonathan R Dimmock、Oludotun A Phillips、Sheri L Wonko、Robert A Hickie、Robert G Tuer、Stephen J Ambrose、R.Stephen Reid、Bulent Mutus、Christopher J Talpas

  DOI：10.1016/0223-5234(89)90002-0

  日期：1989.5
• Synthesis and cytotoxic evaluation of some styryl ketones and related compounds
  作者：JR Dimmock、P Kumar、JW Quail、U Pugazhenthi、J Yang、M Chen、RS Reid、TM Allen、GY Kao、SPC Cole、G Batist、J Balzarini、E De Clercq

  DOI：10.1016/0223-5234(96)88227-4

  日期：1995.1

  A number of 1-aryl-4-methyl-1-penten-3-ones 1 were converted to the corresponding Mannich bases 2 and analogues 3. Attempts to form the azines 4 from several members in series 1 led to the isolation of the corresponding pyrazolines 5 or aryl aldehyde azines 6. Replacement of the isopropyl group of a compound in series 1 by methyl and ethyl functions led to ketones that reacted with hydrazine producing the corresponding azines. The Mannich bases displayed greater activity than the precursor ketones towards murine P388 and L1210 leukemia cells as well as to a panel of human tumour cell lines. Certain of the Mannich bases had selective toxicity towards some human tumour cell lines and others to L1210 cells (in contrast to human T lymphocytes). Several drug-resistant cell lines were shown to be free from cross resistance to a number of the Mannich bases.
• Dimmock; Kumar; Manavathu, Pharmazie, 1994, vol. 49, # 12, p. 909 - 912
  作者：Dimmock、Kumar、Manavathu、Obedeanu、Grewal

  DOI：——

  日期：——
• Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy
  作者：Hongbo Wei、Yun Li、Ke Xiao、Bin Cheng、Huifei Wang、Lin Hu、Hongbin Zhai

  DOI：10.1021/acs.orglett.5b02903

  日期：2015.12.18

  An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6 pi-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.
• Highly Enantioselective Michael Addition of Nitroalkanes to Enones and Its Application in Syntheses of (R)-Baclofen and (R)-Phenibut
  作者：Feng Sha、Xin-Yan Wu、Xing-Tao Guo、Jie Shen

  DOI：10.1055/s-0034-1380203

  日期：——

  enantioselectivities. A highly enantioselective Michael addition of nitroalkanes to α,β-unsaturated ketones was developed. In the presence of a chiral primary amine–thiourea catalyst based on dehydroabietic amine, γ-nitro ketones were obtained with excellent enantioselectivities (up to 99% ee) and in up to 96% yield. This protocol was successfully applied in asymmetric syntheses of (R)-baclofen and (R)-phenibut

  摘要 开发了对α，β-不饱和酮的硝基烷烃的高对映选择性迈克尔加成反应。在基于脱氢松香胺的手性伯胺-硫脲催化剂的存在下，可获得具有出色的对映选择性（高达99％ee）和高达96％收率的γ-硝基酮。该方案已成功用于（R）-baclofen和（R）-pheni的不对称合成中，但收率高且对映选择性优异。 开发了对α，β-不饱和酮的硝基烷烃的高对映选择性迈克尔加成反应。在基于脱氢松香胺的手性伯胺-硫脲催化剂的存在下，可获得具有出色的对映选择性（高达99％ee）和高达96％收率的γ-硝基酮。该方案已成功用于（R）-baclofen和（R）-pheni的不对称合成中，但收率高且对映选择性优异。