cis-4-methoxy-2-(1-propenyl)phenol | 98755-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: cis-4-methoxy-2-(1-propenyl)phenol
• 英文别名: Z-4-methoxy-2-propenylbenzene；cis-pseudoisoeugenol；4-methoxy-2-(1-propenyl)phenol；4-methoxy-2-[(Z)-prop-1-enyl]phenol
• CAS: 98755-19-2
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: CNTCZYAGRDSWBW-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基丁酰氯 、 cis-4-methoxy-2-(1-propenyl)phenol 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 cis-epoxypseudoisoeugenyl 2-methylbutyrate
  参考文献：
  名称：

  Essential oils from hairy root cultures and from fruits and roots of Pimpinella anisum

  摘要：

  Hairy root cultures of Pimpinella anisum were established following inoculation of aseptically grown plantlets with an A(4) pRiA(4) 70 GUS strain of Agrobacterium rhizogenes. The essential oils from the hairy roots, maintained in four different media, and from the fruits and roots of the parent plant were analysed and their compositions compared by GC and GC-mass spectrometry. The major components of the essential oils from the hairy root cultures were trans-epoxypseudoisoeugenyl 2-methylbutyrate, geijerene, pregeijerene, zingiberene and beta-bisabolene, in varying amounts depending on the light or dark growth conditions and on the culture media tested. trans-Epoxypseudoisoeugenyl 2-methylbutyrate, beta-bisabolene and pregeijerene were the major components of the essential oil from the roots of the parent plant, whereas the main component of the fruit oil was trans-anethole. Geijerenes were not detected in the fruit oil. The essential oil yield of the transformed roots grown in one of the media was comparable with that obtained for the roots of the parent plant and, calculated on a dry weight basis, the oil yield of these hairy roots was comparable with that of the fruits. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00022-3
• 作为产物：
  描述：

  4-烯丙氧基苯甲醚 在 sodium t-butanolate 作用下， 以 二甲基亚砜 、 N,N-二甲基苯胺 为溶剂， 反应 12.0h， 生成 cis-4-methoxy-2-(1-propenyl)phenol
  参考文献：
  名称：

  银催化的2,3-二氢苯并呋喃的不对称合成：一种新的手性翼龙合成。

  摘要：

  2,3-二氢苯并呋喃可以在Ag（I）配合物的催化下，在氟离子源的存在下，通过芳族醛与2,3-二氢苯并西拉西平的缩合，非对映选择性地制备。通过使用手性催化剂应用该策略导致了天然顺式-罗汉果及其反式异构体的新的对映选择性全合成。通过该方法，实现了抗真菌剂（-）-罗哌卡丁的首次对映选择性全合成。另外，还提出了新的进入2，5-二氢苯并己平杂芳族体系的方法。

  DOI：

  10.1002/chem.200600332

文献信息

• A concise and diastereoselective total synthesis of cis and trans-pterocarpans
  作者：Leticia Jiménez-González、Míriam Álvarez-Corral、Manuel Muñoz-Dorado、Ignacio Rodríguez-García

  DOI：10.1039/b500919g

  日期：——

  A new strategy for the diastereoselective and convergent synthesis of pterocarpans which is able to control the relative stereochemistry of the molecule through allylation of aromatic aldehydes with cyclic allylsiloxanes is described.

  描述了一种新的策略，用于二面角选择性和收敛合成羽扇豆素，该策略能够通过芳香醛与环状烯丙基硅氧烷的烯丙基化来控制分子的相对立体化学。
• Oxiranylphenyl esters from Pimpinella diversifolia
  作者：Albert T. Bottini、Vasu Dev、David J. Garfagnoli、C.S. Mathela、A.B. Melkani、Angela A. Miller、Noel S. Sturm

  DOI：10.1016/s0031-9422(00)94530-8

  日期：1985.12

  Region of India, have been identified as the (+)-Z-2-methyl-2-butenoate (angelate) and (+)-isobutyrate esters of 4-methoxy-2-(E-3-methyloxiranyl)phenol. Aromatic 13C NMR resonances of these compounds and their synthetic acetate analog, as well as those of 2-methoxy-4-(E-3-methyloxiranyl)phenyl acetate prepared from isoeugenol, were found to be in excellent agreement with calculated values. Comparison of

  摘要 采集于印度 Kumaun 地区的 Pimpinella diversifolia 根部精油的主要成分已被鉴定为 (+)-Z-2-methyl-2-butenoate (angelate) 和 (+)-isobutyrate 酯。 4-甲氧基-2-(E-3-甲基环氧乙烷基)苯酚。发现这些化合物及其合成乙酸酯类似物的芳族 13C NMR 共振以及由异丁香酚制备的 2-甲氧基-4-（E-3-甲基环氧乙烷基）苯乙酸酯的共振与计算值非常吻合。天然和合成产物的 EIMS 与先前鉴定为 2-甲氧基-4-(E-3-甲基环氧乙烷基)苯基酯的化合物的 EIMS 比较表明它们也具有 4-甲氧基-2-(E-3-甲基环氧乙烷基)苯基结构。
• Silver-Catalyzed Asymmetric Synthesis of 2,3-Dihydrobenzofurans: A New Chiral Synthesis of Pterocarpans
  作者：Leticia Jiménez-González、Sergio García-Muñoz、Miriam Álvarez-Corral、Manuel Muñoz-Dorado、Ignacio Rodríguez-García

  DOI：10.1002/chem.200600332

  日期：2006.11.24

  of fluoride ion. The application of this strategy by using chiral catalysts leads to a new enantioselective total synthesis of natural cis-pterocarpans and their trans isomers. Through this method, the first enantioselective total synthesis of the antifungal agent (-)-pterocarpin was achieved. In addition, a new entry into the heteroaromatic system of 2,5-dihydrobenzoxepine is also presented.

  2,3-二氢苯并呋喃可以在Ag（I）配合物的催化下，在氟离子源的存在下，通过芳族醛与2,3-二氢苯并西拉西平的缩合，非对映选择性地制备。通过使用手性催化剂应用该策略导致了天然顺式-罗汉果及其反式异构体的新的对映选择性全合成。通过该方法，实现了抗真菌剂（-）-罗哌卡丁的首次对映选择性全合成。另外，还提出了新的进入2，5-二氢苯并己平杂芳族体系的方法。
• Essential oils from hairy root cultures and from fruits and roots of Pimpinella anisum
  作者：Paula M. Santos、A.Cristina Figueiredo、M.Margarida Oliveira、JoséG. Barroso、Luis G. Pedro、Stanley G. Deans、A.K.M. Younus、Johannes J.C. Scheffer

  DOI：10.1016/s0031-9422(98)00022-3

  日期：1998.6

  Hairy root cultures of Pimpinella anisum were established following inoculation of aseptically grown plantlets with an A(4) pRiA(4) 70 GUS strain of Agrobacterium rhizogenes. The essential oils from the hairy roots, maintained in four different media, and from the fruits and roots of the parent plant were analysed and their compositions compared by GC and GC-mass spectrometry. The major components of the essential oils from the hairy root cultures were trans-epoxypseudoisoeugenyl 2-methylbutyrate, geijerene, pregeijerene, zingiberene and beta-bisabolene, in varying amounts depending on the light or dark growth conditions and on the culture media tested. trans-Epoxypseudoisoeugenyl 2-methylbutyrate, beta-bisabolene and pregeijerene were the major components of the essential oil from the roots of the parent plant, whereas the main component of the fruit oil was trans-anethole. Geijerenes were not detected in the fruit oil. The essential oil yield of the transformed roots grown in one of the media was comparable with that obtained for the roots of the parent plant and, calculated on a dry weight basis, the oil yield of these hairy roots was comparable with that of the fruits. (C) 1998 Elsevier Science Ltd. All rights reserved.