(E)-1-(3-(benzyloxy)prop-1-en-1-yl)-4-bromobenzene | 157035-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(3-(benzyloxy)prop-1-en-1-yl)-4-bromobenzene
• 英文别名: 1-bromo-4-[(E)-3-phenylmethoxyprop-1-enyl]benzene
• CAS: 157035-13-7
• 化学式: C₁₆H₁₅BrO
• 分子量: 303.198
• InChiKey: ZZRQTFOHOHLGCT-QPJJXVBHSA-N

物化性质

• 沸点：
  406.0±33.0 °C(predicted)
• 密度：
  1.317±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-(benzyloxy)prop-1-en-1-yl)-4-bromobenzene 在 咪唑 、 lithium hydroxide 、 copper(I) bromide dimethylsulfide complex 、 二异丁基氢化铝 、 potassium carbonate 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 30.17h， 生成 13-[Tert-butyl(dimethyl)silyl]oxy-4-methoxy-2,11-dioxatricyclo[13.2.2.13,7]icosa-1(17),3,5,7(20),15,18-hexaen-10-one
  参考文献：
  名称：

  Total Synthesis of Combretastatins D

  摘要：

  The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construction of both combretastatins. The synthesis of combretastatin D-2 is completed by the use of Sammuelson's dehydroxylation protocol, The asymmetric epoxide of combretastatin D-1 is constructed in two separate operations: one asymmetric center is fixed at an early stage of the synthetic route by Sharpless AD of a trans-styrene derivative, inducing the intramolecular formation of the asymmetric epoxide at the final stages. The synthesis of the title compounds is accomplished in high overall yields (37% for D-1 and 41% for D-2, 9 steps in both cases). X-ray crystallographic analysis of the (S)-(+) acetylmandelic ester of (-)-combretastatin D-1 verified its revised structure.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<33::aid-chem33>3.0.co;2-8
• 作为产物：
  描述：

  反式-4-溴肉桂酸乙酯 在 四丁基碘化铵 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 3.83h， 生成 (E)-1-(3-(benzyloxy)prop-1-en-1-yl)-4-bromobenzene
  参考文献：
  名称：

  Synthesis of combretastatin D-2. An efficient route to caffrane macrolactones

  摘要：

  Combretastatin D-2, (1), was synthesized via a 10 step sequence. Macrolactonization was performed on saturated substrate 12 in high yield and the double bond was established via dehalogenation of intermediate 15.

  DOI：

  10.1016/s0040-4039(00)73369-7

文献信息

• Diastereoselective Borocyclopropanation of Allylic Ethers Using a Boromethylzinc Carbenoid
  作者：Guillaume Benoit、André B. Charette

  DOI：10.1021/jacs.6b09090

  日期：2017.2.1

  borocyclopropanation of (E)- and (Z)-allylic ethers and styrene derivatives via the Simmons-Smith reaction using a novel boromethylzinc carbenoid is described. The carbenoid precursor is prepared via a 3-step sequence from inexpensive and commercially available starting materials. This methodology allows for the preparation of 1,2,3-substituted borocyclopropanes in high yields and diastereoselectivities

  描述了 (E)-和 (Z)-烯丙基醚和苯乙烯衍生物通过 Simmons-Smith 反应使用新型硼甲基锌卡宾进行硼环丙烷化。卡宾前体是通过 3 步序列从廉价且市售的起始材料制备的。这种方法允许以高产率和非对映选择性制备 1,2,3-取代的硼环丙烷。还进行了几个后功能化反应来说明这些构建块的多功能性。
• Diastereoselective synthesis of tetrahydropyranes <i>via</i> Ag(<scp>i</scp>)-initiated dimerization of cinnamyl ethers
  作者：Davide Ruggeri、Elena Motti、Nicola Della Ca’、Giovanni Maestri

  DOI：10.1039/d2ob01876d

  日期：——

  We present herein the first synthesis of tetrahydropyranes promoted by a silver salt. Cinnamyl ethers undergo a formal dimerization affording the target heterocycle via sequential C–O bond cleavage/C–H bond functionalization. The cascade allows one to assemble three new bonds and to establish up to four stereocenters. The reaction likely proceeds through a cationic manifold that forms the target in

  我们在此介绍了由银盐促进的四氢吡喃的首次合成。肉桂基醚通过连续的 C-O 键断裂/C-H 键功能化进行形式二聚，得到目标杂环。级联允许一个人组装三个新键并建立多达四个立体中心。反应可能通过以非对映选择性方式形成目标的阳离子歧管进行。
• Rapid and Safe Continuous‐Flow Simmons‐Smith Cyclopropanation using a Zn/Cu Couple Column
  作者：José Luis Nova‐Fernández、Gustavo Pascual‐Coca、Silvia Cabrera、José Alemán

  DOI：10.1002/adsc.202300665

  日期：2024.2.20

  zinc-copper couple.8 Over the years, several modifications have taken place, substituting either the metal alloy by diethylzinc,9 or the dihalogenated species by a diazo derivative.10 Scheme 1 Open in figure viewerPowerPoint a. Classical Simmons-Smith reaction conditions and its variations through time. b. Semi-flow cyclopropanation using diazo derivatives. c. This work. Although the transformation presents

  过去几十年来，流动化学实验方案的相关性和重要性不断增强，最近发表的有关该领域的越来越多的研究就证明了这一点。1许多众所周知的转变已从间歇式转变为流动式，2因为（微）反应器的使用提供了不同的优势，例如更好的传热和传质或改进对敏感和高活性物质的处理。3对于后一种情况，连续流装置的使用带来了一种非常有用的方式，可以扩大依赖于敏感、反应性或短时活物种的过程。这种化合物的直接在线使用实现了使用批量方法无法实现的新转变，同时减少了危害和废物产生。4 从这个意义上说，使用填充有非均相催化剂和试剂的盒可以更有效地处理危险或反应性物质。由于流量设置通常依赖于内部体积非常小的（微）反应器，因此一次仅混合少量试剂，避免了处理大量反应性、腐蚀性或爆炸性物质的危险。5此外，在过去几年中，填充不同金属的盒已被提出用于多种有机转化，其中完成了敏感有机金属物质的原位生产。6 另一方面，Simmons-Smith 反应是从
• Total Synthesis of Combretastatins D
  作者：Elias A. Couladouros、Ioanna C. Soufli、Vassilios I. Moutsos、Raj K. Chadha

  DOI：10.1002/(sici)1521-3765(199801)4:1<33::aid-chem33>3.0.co;2-8

  日期：1998.1

  The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construction of both combretastatins. The synthesis of combretastatin D-2 is completed by the use of Sammuelson's dehydroxylation protocol, The asymmetric epoxide of combretastatin D-1 is constructed in two separate operations: one asymmetric center is fixed at an early stage of the synthetic route by Sharpless AD of a trans-styrene derivative, inducing the intramolecular formation of the asymmetric epoxide at the final stages. The synthesis of the title compounds is accomplished in high overall yields (37% for D-1 and 41% for D-2, 9 steps in both cases). X-ray crystallographic analysis of the (S)-(+) acetylmandelic ester of (-)-combretastatin D-1 verified its revised structure.
• Synthesis of combretastatin D-2. An efficient route to caffrane macrolactones
  作者：Elias A. Couladouros、Ioanna C. Soufli

  DOI：10.1016/s0040-4039(00)73369-7

  日期：1994.6

  Combretastatin D-2, (1), was synthesized via a 10 step sequence. Macrolactonization was performed on saturated substrate 12 in high yield and the double bond was established via dehalogenation of intermediate 15.