(E)-3-(1,3-dihydroisobenzofuran-5-yl)-1-phenylprop-2-en-1-ol | 501120-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-3-(1,3-dihydroisobenzofuran-5-yl)-1-phenylprop-2-en-1-ol
• 英文别名: (E)-3-(1,3-benzodioxol-5-yl)-1-phenylprop-2-en-1-ol
• CAS: 501120-45-2
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: DWAJGCGUJQAWBK-SOFGYWHQSA-N

物化性质

• 沸点：
  431.3±14.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(1,3-dihydroisobenzofuran-5-yl)-1-phenylprop-2-en-1-ol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以252 mg的产率得到5-(3-bromo-4-phenyloxetan-2-yl)benzo[1,3]dioxole
  参考文献：
  名称：

  国家统计局介导的环化反式-肉桂醇

  摘要：

  通过NaBH 4介导的查耳酮3还原反应，再由NBS介导的亲电反应，从功能化的查耳酮3中开发出一种有效，直接的三步合成路线，以2,4-二取代-3-溴氧杂环丁烷5为反式-反式连续立体中心。以高收率将所得反式肉桂醇4环化。骨架3是通过Claisen-Schmidt缩合取代的芳基醛1和芳基甲基酮或叔丁基甲基酮2制备的。合成路线获得了高收率，并且整个反应过程仅花费了一天。研究了骨架3的取代作用，各种反应条件和合理的机理。

  DOI：

  10.1016/j.tet.2013.05.110
• 作为产物：
  描述：

  (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-phenylprop-2-en-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以92%的产率得到(E)-3-(1,3-dihydroisobenzofuran-5-yl)-1-phenylprop-2-en-1-ol
  参考文献：
  名称：

  InCl 3 -NaBH 4试剂系统还原活化的共轭烯烃

  摘要：

  乙腈中催化量的氯化铟（III）和硼氢化钠的组合可选择性降低共轭烯烃（如α，α-二氰基烯烃，α，β-不饱和腈，氰基酯，氰基膦酸酯和二羧酸酯）中的碳-碳双键。但是，减少查耳酮几乎没有什么不同。如果将反应混合物用H 2 O淬灭，则它们会还原为饱和酮和醇的混合物，而用MeOH淬灭只会产生饱和醇。

  DOI：

  10.1016/j.tet.2003.08.022

文献信息

• Copper-Catalyzed Oxidative Transformation of Secondary Alcohols to 1,5-Disubstituted Tetrazoles
  作者：Balaji V. Rokade、Karthik Gadde、Kandikere Ramaiah Prabhu

  DOI：10.1002/adsc.201300863

  日期：2014.3.24

  A mild and convenient oxidative transformation of secondary alcohols to 1,5‐disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)2.6 H2O] (5 mol%) and 2,3‐dichloro‐5,6‐dicyano‐para‐benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient

  在催化量的高氯酸铜（II）六水合物[Cu（ClO 4）]存在下，通过使用三甲基叠氮化硅（TMSN 3）作为氮源，发现了中等程度的醇向1,5-二取代的四唑进行温和且方便的氧化转化。2 。6 H 2 O]（5 mol％）和2,3-二氯-5,6-二氰基对苯醌（DDQ）（1.2当量）作为氧化剂。该反应在环境条件下进行，并通过CC键裂解进行。
• Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether
  作者：Madala Hari Babu、Gadi Ranjith Kumar、Ruchir Kant、Maddi Sridhar Reddy

  DOI：10.1039/c6cc10256e

  日期：——

  Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units.

  首次实现了使用廉价的催化体系以区域选择性和立体选择性的方式将芳基硼酸加成到系链的乙炔基上，从而获得了备受追捧的烯丙基/均烯丙基醇/胺单元。
• Asymmetric epoxidation via phase-transfer catalysis: direct conversion of allylic alcohols into α,β-epoxyketones
  作者：Barry Lygo、Daniel C. M. To

  DOI：10.1039/b206530d

  日期：——

  Studies into the use of a chiral phase-transfer catalyst in conjunction with sodium hypochlorite to effect the enantio-selective formation of alpha,beta-epoxyketones from allylic alcohols are described.

  描述了使用手性相转移催化剂与次氯酸钠结合以实现烯丙基醇对映选择性形成α，β-环氧酮的研究。
• Iodine-catalyzed allylic alkylation of sulfonamides and carbamates with allylic alcohols at room temperature
  作者：Wenhan Wu、Weidong Rao、Ya Qin Er、Joanna Kejun Loh、Chai Yun Poh、Philip Wai Hong Chan

  DOI：10.1016/j.tetlet.2008.02.079

  日期：2008.4

  A highly efficient iodine-catalyzed allylic alkylation of a wide variety of sulfonamides and carbamates with allylic alcohols is reported herein. The reaction is operationally straightforward and proceeds under very mild conditions at room temperature in good to excellent yields (up to 99%). (C) 2008 Elsevier Ltd. All rights reserved.
• Efficient chemoselective biohydrogenation of 1,3-diaryl-2-propen-1-ones catalyzed by Saccharomyces cerevisiae yeasts in biphasic system
  作者：Vanessa Dutra Silva、Boris Ugarte Stambuk、Maria da Graça Nascimento

  DOI：10.1016/j.molcatb.2010.01.010

  日期：2010.5

  A series of chalcones (1-9) was synthesized by base catalyzed aldol condensation with 50-94% yields. These alpha,beta-unsaturated carbonyl compounds were used as substrates in biotransformation reactions mediated by three industrial Saccharomyces cerevisiae strains in biphasic systems. Several reaction parameters were evaluated, such as yeast concentration, temperature, pH, substrate concentration, organic solvent, volume of aqueous and organic phases and the influence of substituent groups on chalcones 1-9. The biotransformation was chemoselective and formed only the corresponding saturated ketones. The highest conversion (>99%) to the dihydrochalcone was obtained at 30-45 degrees C and pH above 5.5, while the cellular and substrate concentrations also showed a strong influence on the biohydrogenation reaction. Organic solvents with log P >3.2 (hexane or heptane) were the most appropriate, and 40-80% of aqueous phase allowed the highest conversions probably by maintaining the yeast enzymes catalytically active. The influence of substituents on rings A and B of chalcones 1-9 was low and no correlation between the donor or withdrawing electron groups was observed. (C) 2010 Elsevier B.V. All rights reserved.