5-<3-(4-methoxyphenyl)-2-propenyl>-1,3-benzodioxol-6-ol | 138958-75-5

• 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: 5-<3-(4-methoxyphenyl)-2-propenyl>-1,3-benzodioxol-6-ol
• 英文别名: (E)-6-(3-(4-methoxyphenyl)allyl)benzo[d][1,3]dioxol-5-ol；6-[(E)-3-(4-methoxyphenyl)prop-2-enyl]-1,3-benzodioxol-5-ol
• CAS: 138958-75-5
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: XLRPTZOSPSWDRH-NSCUHMNNSA-N

物化性质

• 沸点：
  470.8±45.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-<3-(4-methoxyphenyl)-2-propenyl>-1,3-benzodioxol-6-ol 在 silver(l) oxide 作用下， 生成 (E)-6-((E)-3-(4-methoxyphenyl)allylidene)benzo[d][1,3]dioxol-5(6H)-one
  参考文献：
  名称：

  通过磺酰基衍生的MIL-101 MOF催化的邻甲醌甲基化物中间体进行的 2 H-苯甲基二聚体轻松实现†

  摘要：

  MIL-101–SO 3 H MOF是使用市售材料合成的。合成后的MIL-101-SO 3 H的特征在于SEM，XRD，FTIR，BET和TGA。使用磺酰基衍生的MIL-101 MOF作为催化剂，可实现2 H-苯甲基二烯催化的高效非对映选择性均二聚。在温和的催化反应条件下，以高收率和非对映选择性生成了苯并吡喃并苯并吡喃多环结构。此外，当2 H-色烯带有不同的取代基时，观察到一个区域异构体，从而提供了chromeno [2,3- b] chromene二聚体，收率高，非对映选择性好。提出了一种具有串联重排/杂-Diels-Alder反应序列的机制，这得到了证据的支持。此外，酸性MIL-101 MOF催化剂可以循环使用十次，而不会影响收率和选择性。

  DOI：

  10.1039/c8nj01354c
• 作为产物：
  描述：

  芝麻酚 、 1'-羟基草蒿脑 在 柠檬酸 、 维生素 C 作用下， 以 水 为溶剂， 反应 4.0h， 以45.5 g的产率得到5-<3-(4-methoxyphenyl)-2-propenyl>-1,3-benzodioxol-6-ol
  参考文献：
  名称：

  Synthesis of alkoxy-substituted diaryl compounds and correlation of ring separation with inhibition of tubulin polymerization: differential enhancement of inhibitory effects under suboptimal polymerization reaction conditions

  摘要：

  A number of cytostatic compounds (2-4, 7, and 8), which can be described as ''diaryl'', inhibit tubulin polymerization, cause cells to accumulate in mitotic arrest, and competitively inhibit the binding of colchicine to tubulin. They differ, however, in the separation of the two aryl moieties. To attempt to understand this variability we prepared a series of analogues modeled on 3 and 4 (''benzodioxole series'') and on 7 and 8 (''combretastatin series'') which differed only in the number of methylene units (ranging from none to four) separating the aryl moieties. These compounds were evaluated for their effects on tubulin polymerization, colchicine binding, and the growth of L1210 murine leukemia cells. In terms of inhibitory effects on tubulin polymerization, for the combretastatin series there was an optimal separation of the two phenyl rings by a two-carbon bridge (compound 24), with progressively decreasing inhibitory activity when the separation was by one carbon (20), three carbons (25), or four carbons (28) (the biphenyl analogue 16 was inactive). The benzodioxole series, however, did not permit us to generalize this finding, because the least active agents prepared (39 and 40) had a two-carbon bridge, while those with one- (5 and 6) and three-carbon (46 and 47) bridges were nearly equivalent in potency. Submicromolar IC50 values for inhibition of L1210 cell growth were only obtained for compounds 20 (IC50, 0.2-mu-M), 24 (0.07-mu-M), and 25 (0.4-mu-M). While evaluating the effects of these agents on tubulin polymerization, we noted with the combretastatin series and with several standard agents that apparent potency (in terms of IC50 values) was always lower if the reaction was performed at 30-degrees-C, with 0.25 mM MgCl2, than at 37-degrees-C, with 1.0 mM MgCl2. This enhancement of IC50 values in the former system as compared with the latter was particularly dramatic for the less active agents (e.g., 28) as compared with the more active (e.g. 24).

  DOI：

  10.1021/jm00084a011

文献信息

• Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile
  作者：Alafate Adili、Zhong-Lin Tao、Dian-Feng Chen、Zhi-Yong Han

  DOI：10.1039/c4ob02602k

  日期：——

  2-Amino-3-cyano-4H-chromenes show great potential as novel anticancer agents. Here we report a quinine-catalyzed highly enantioselective formal 4 + 2 cycloaddition of ortho-quinone methides and malononitrile, providing a unique approach to 4-arylvinyl, 4-aryl and 4-vinyl 2-amino-3-cyano-4H-chromenes with excellent yields and enantioselectivities.

  2-氨基-3-氰基-4H-色酮显示出作为新型抗癌药物的巨大潜力。在这里，我们报告了奎宁催化的高度对映选择性的正式4 + 2环加成，将邻醌甲烯和丙二腈进行反应，提供了一种独特的方法来合成4-芳基乙烯基，4-芳基和4-乙烯基2-氨基-3-氰基-4H-色酮，产率和对映选择性均非常优异。
• Enantioselective Addition of Boronates to <i>o</i>-Quinone Methides Catalyzed by Chiral Biphenols
  作者：Yi Luan、Scott E. Schaus

  DOI：10.1021/ja309076g

  日期：2012.12.12

  Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3'-Br(2)-BINOL. A two-step synthesis of (S)-4-methoxydalbergione in good yield and selectivity was achieved.

  发现手性双酚催化芳基或链烯基硼酸酯与邻醌甲基化物的对映选择性不对称加成。在 10 mol% 3,3'-Br(2)-BINOL 存在下，以高对映体比（高达 98:2）获得了高产率（高达 95%）的取代 2-苯乙烯基苯酚。以良好的产率和选择性实现了 (S)-4-甲氧基丹参的两步合成。
• Catalytic Asymmetric [4+1] Cyclization of <i>ortho</i> -Quinone Methides with 3-Chlorooxindoles
  作者：Xiao-Li Jiang、Si-Jia Liu、Yu-Qi Gu、Guang-Jian Mei、Feng Shi

  DOI：10.1002/adsc.201700487

  日期：2017.10.4

  In this work, we established catalytic asymmetric [4+1] cyclization of ortho‐quinone methides (o‐QMs) with 3‐chlorooxindoles and a catalytic asymmetric domino oxidation/[4+1] cyclization reaction of 2‐alkylphenols with 3‐chlorooxindoles, which constructed a spirooxindole‐based 2,3‐dihydrobenzofuran scaffold in good yield (up to 97%), with excellent diastereoselectivity (up to >95:5 dr) and high enantioselectivity

  在这项工作中，我们建立了带有3-氯氧吲哚的邻醌甲基化物（o -QMs）的催化不对称[4 + 1]环化和2-烷基酚与3-氯氧吲哚的催化不对称多米诺氧化/ [4 + 1]环化反应。 ，以高产率（高达97％），优异的非对映选择性（高达> 95：5 dr）和高对映选择性（高达ee高达99％）构建了基于螺氧杂吲哚的2,3-二氢苯并呋喃支架。此工作不仅第一高度对映选择性[4 + 1]的环化ö -QMs但也实现了第一催化不对称多米诺[4 + 1]的环化ö-QMs。此外，这两种反应均提供了高效的立体选择性方法，可用于构建具有光学纯度的基于螺氧吲哚的2,3-二氢苯并呋喃支架。
• Enantioselective one-pot synthesis of 2-amino-4<i>H</i>-chromenes via C−H oxidation and Michael addition/ring closure sequences
  作者：Kyeong Seop Kim、Dae Young Kim

  DOI：10.1080/00397911.2021.2024572

  日期：2022.1.17

  Abstract The chiral 2-amino-4H-chromene derivatives were obtained from 2-alkyl-substituted phenol derivatives in moderate to high yields with excellent enantioselectivities through one-pot cascade via C–H oxidation/Michael addition/ring closure sequences using a binaphthyl-modified organocatalyst with low catalyst loading (1.25 mol%).

  摘要 手性 2-氨基-4 H-色烯衍生物由 2-烷基取代的苯酚衍生物通过一锅级联通过 C-H 氧化/迈克尔加成/使用联萘的闭环序列以中等至高产率获得，具有优异的对映选择性。具有低催化剂负载量（1.25 mol％）的改性有机催化剂。
• Iron-Catalyzed Rearrangements and Cycloaddition Reactions of 2<i>H</i>-Chromenes
  作者：Yi Luan、Huan Sun、Scott E. Schaus

  DOI：10.1021/ol202772k

  日期：2011.12.16

  Iron(III) salts catalyze the tandem rearrangement/hetero-Diels-Alder reaction of 2H-chromenes to yield tetrahydrochromeno heterocycles. The process can occur as a homodimerization and cycloaddition process using electron-rich dienophiles. Deuterium labeling and mechanistic studies revealed a hydride shift and ortho-quinone methide cycloaddition reaction pathway.