3-(3-chlorophenyl)-1-phenylpropan-1-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(3-chlorophenyl)-1-phenylpropan-1-ol
• 化学式: C₁₅H₁₅ClO
• mdl: MFCD16517494
• 分子量: 246.737
• InChiKey: BECOIFQFYNUSCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(3-chlorophenyl)-1-phenylpropan-1-ol 在 N-羟基邻苯二甲酰亚胺 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 O-(3-(3-chlorophenyl)-1-phenylpropyl)hydroxylamine
  参考文献：
  名称：

  Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase

  摘要：

  Tryptophan (Trp) catabolizing enzymes play an important and complex role in the development of cancer. Significant evidence implicates them in a range of inflammatory and immunosuppressive activities. Whereas inhibitors of indoleamine 2,3-dioxygenase-1 (IDO1) have been reported and analyzed in the clinic, fewer inhibitors have been described for tryptophan dioxygenase (TDO) and indoleamine 2,3-dioxygenase-2 (IDO2) which also have been implicated more recently in cancer, inflammation and immune control. Consequently the development of dual or pan inhibitors of these Trp catabolizing enzymes may represent a therapeutically important area of research. This is the first report to describe the development of dual and pan inhibitors of IDO1, TDO and IDO2. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.010
• 作为产物：
  描述：

  苯甲醇 在 chromium(III) chloride hexahydrate 、 C₁₉H₁₅Cl₃CrN₃ 、 sodium t-butanolate 作用下， 140.0 ℃ 、137.9 kPa 条件下， 反应 13.5h， 生成 3-(3-chlorophenyl)-1-phenylpropan-1-ol
  参考文献：
  名称：

  氯化铬催化仲醇的格尔伯特型β-烷基化及其相应的NNN钳形配合物

  摘要：

  仲醇的β-烷基化使用地球上丰富、廉价和环境友好的 3 d过渡金属铬盐 CrCl 3及其相应的钳形铬络合物 ( Ph2 NNN)CrCl 3 (0.005 mol%) 在 140° 下成功完成在 NaO t Bu (5 mol%)存在下，在常规（3 小时）和微波加热条件下（约75 W，1.5 小时）下空气中的 C。与常规加热（84% 产率和 16 800 TON 在 5600 TOh -1 ）相比，微波条件提供了更好的结果（90% 产率和 18 000 TON 在 12 000 TOh -1）。而 CrCl 3 (0.005 mol%) 提供 76% 的产率（在 10 133 TOh 时为 15 200 TON-1 ) β-烷基化产物在微波条件下在 5 mol% NaO t Bu 存在下，相应的钳形铬络合物 ( Ph2 NNN)CrCl 3 (0.005 mol%) 产生 90% 的产率 (18

  DOI：

  10.1039/d2cy00759b

文献信息

• One-pot β-alkylation of secondary alcohols with primary alcohols catalyzed by ruthenacycles
  作者：Xu Chang、Low Wei Chuan、Li Yongxin、Sumod A. Pullarkat

  DOI：10.1016/j.tetlet.2012.01.025

  日期：2012.3

  best combination of reactivity and product selectivity among the four. An expanded scope of substrates was also studied with the inclusion of unsaturated primary alcohols. The reactivity trend observed gave insights into the role of hydrogen bonding in the catalytic mechanism involving transfer hydrogenation between the substrates and the transition metal catalyst.

  描述了钌醇循环催化的仲醇与伯醇的一锅式β-烷基化。四个C-N螯合物的调查ruthenacycles经由苯基甲胺的环金属化反应，合成Ñ -methylphenylmethanamine，Ñ，Ñ -dimethylphenylmethanamine，和萘-1-基甲胺与[（η 6 -C 6 H ^ 6）的RuCl 2 ] 2进行了。发现所有四种配合物均与基于苯甲胺的钌环烷有活性，显示出这四种反应性和产物选择性的最佳组合。还研究了包括不饱和伯醇在内的底物的扩大范围。观察到的反应性趋势使人们深入了解了氢键在涉及底物和过渡金属催化剂之间转移加氢的催化机理中的作用。
• Catalyst-Free Dehydrative α-Alkylation of Ketones with Alcohols: Green and Selective Autocatalyzed Synthesis of Alcohols and Ketones
  作者：Qing Xu、Jianhui Chen、Haiwen Tian、Xueqin Yuan、Shuangyan Li、Chongkuan Zhou、Jianping Liu

  DOI：10.1002/anie.201308642

  日期：2014.1.3

  Direct dehydrative α‐alkylation reactions of ketones with alcohols are now realized under simple, practical, and green conditions without using external catalysts. These catalyst‐free autocatalyzed alkylation methods can efficiently afford useful alkylated ketone or alcohol products in a one‐pot manner and on a large scale by CC bond formation of the in situ generated intermediates with subsequent

  现在，在简单，实用和绿色的条件下，无需使用外部催化剂即可实现酮与醇的直接α-烷基脱水反应。这些无催化剂的自动催化烷基化方法可以通过原位生成的中间体的CC键形成以及随后可控和选择性的Meerwein–Pondorf–Verley– Oppenauer型氧化还原工艺。
• Selective C‐alkylation Between Alcohols Catalyzed by N‐Heterocyclic Carbene Molybdenum
  作者：Jiahao Liu、Weikang Li、Yinwu Li、Yan Liu、Zhuofeng Ke

  DOI：10.1002/asia.202100959

  日期：2021.10.18

  The first molybdenum-catalyzed C-alkylation between alcohols via borrowing hydrogen is reported.

  报道了第一个钼催化的醇之间通过借氢进行的 C-烷基化反应。
• Manganese-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols under Phosphine-Free Conditions
  作者：Tingting Liu、Liandi Wang、Kaikai Wu、Zhengkun Yu

  DOI：10.1021/acscatal.8b01960

  日期：2018.8.3

  secondary alcohols with primary alcohols under phosphine-free conditions. The β-alkylated secondary alcohols were obtained in moderate to good yields with water formed as the byproduct through a borrowing hydrogen pathway. β-Alkylation of cholesterols was also effectively achieved. The present protocol provides a concise atom-economical method for C–C bond formation from primary and secondary alcohols.

  在无膦条件下，带有吡啶基负载的吡唑基-咪唑基配体的锰（I）配合物可有效催化仲醇与伯醇的直接β-烷基化。β-烷基化的仲醇以中等至良好的产率获得，其中通过借用的氢途径形成副产物水。胆固醇的β-烷基化也得到有效实现。本协议为从伯醇和仲醇形成C-C键提供了一种简明的原子经济方法。
• Transition metal complexes of a bis(carbene) ligand featuring 1,2,4-triazolin-5-ylidene donors: structural diversity and catalytic applications
  作者：Vivek Kumar Singh、S. N. R. Donthireddy、Praseetha Mathoor Illam、Arnab Rit

  DOI：10.1039/d0dt02142c

  日期：——

  [Ir(Cp*)Cl2]2 to generate a doubly C–H activated IrIII–NHC complex 5. Similarly, the triazolinylidene donor supported diorthometalated RuII-complex 6 is also obtained. Complexes 5 and 6 represent the first examples of a stable diorthometalated binuclear IrIII/RuII-complex supported by 1,2,4-triazolin-5-ylidene donors. The synthesized IrIII–NHC complex 5 is found to be more effective than its RuII-analogue

  1,3-双（1,2,4-三唑-1-基）苯与溴乙烷的二烷基化反应会导致形成[ L -H 2 ] Br 2，在与NH 4 PF 6进行盐复分解反应后，产生带有非配位抗衡离子的双（三唑鎓）盐[ L -H 2 ]（PF 6）2。[ L -H 2 ]（PF 6）2和Ag 2 O以1：1的比例反应，生成组成为[（L）2 Ag 2 ]（PF 6）的双核Ag I-四碳烯络合物）2与[Cu（SMe 2）Br]进行容易的金属转移反应，生成相应的Cu I -NHC络合物[（L）2 Cu 2 ]（PF 6）2。相比之下，[ L -H 2 ] Br 2与[Ir（Cp *）Cl 2 ] 2反应生成双重CH-活化的Ir III -NHC络合物5。类似地，供体triazolinylidene支持的diorthometalated钌II -配合物6也被获得。配合物5和6代表由1,2,4-三唑啉-5-亚烷基供体支撑的稳定的双原金属化双核Ir