(E)-4-(benzo[d][1',3']dioxol-5'-yl)-but-3-en-2-ol | 130551-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-4-(benzo[d][1',3']dioxol-5'-yl)-but-3-en-2-ol
• 英文别名: 4-(3,4-Methylenedioxyphenyl)-3-buten-2-ol；(E)-4-(1,3-benzodioxol-5-yl)but-3-en-2-ol
• CAS: 130551-29-0
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: BFKJEEFQRZRWBY-NSCUHMNNSA-N

物化性质

• 沸点：
  341.8±11.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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)-4-(benzo[d][1',3']dioxol-5'-yl)-but-3-en-2-ol 在 sodium hydride 、 三氯氧磷 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 5-[(1E,3E,5E)-6-diethoxyphosphorylhexa-1,3,5-trienyl]-1,3-benzodioxole
  参考文献：
  名称：

  A STEREOSELECTIVE SYNTHESIS OF UNSATURATED PHOSPHONATES BY WITTIG-HORNER REACTIONS OF BISPHOSPHONYLMETHANE WITH 5-ARYL-(3-METHYL)-2E,4E-PENTADIENALS

  摘要：

  A new type of unsaturated phosphonates 5 were synthesized by the Wittig-Horner reactions of bisphosphonylmethane 4 with 5-aryl-2(E),4(E)-pentadienal and 5-aryl-3-methyl-2(E), 4(E)-pentadienal. The structures of all new compounds prepared were characterized by H-1 NMR, P-31 NMR, C-13 NMR, IR spectra, MS and elemental analyses, one of them was determined by X-ray diffraction analysis.

  DOI：

  10.1080/10426500008045248
• 作为产物：
  描述：

  (E)-4-(benzo[d][1,3]dioxol-5-yl)but-3-en-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以99%的产率得到(E)-4-(benzo[d][1',3']dioxol-5'-yl)-but-3-en-2-ol
  参考文献：
  名称：

  （E）-4-（2'，5'-二甲基苯基）-but-3-en-2-ol和（E）-4-（benzo [ d ] [1'，3'] dioxol-5的动力学拆分脂肪酶催化的酯交换反应合成'-基）-丁-3-烯-2-醇

  摘要：

  开发了一种短而有效的化学酶促途径，以生产两种立体异构形式的烯丙醇，其在立体异构中心具有庞大的芳族取代基，即（E）-4-（2'，5'-二甲基苯基）-but-3-en-2 -ol和（E）-4-（苯并[ d ] [1'，3']二恶醇-5'-基）-丁-3-烯-2-醇。醇经过脂肪酶催化的酯交换反应，南极假丝酵母（CAL-B）的脂肪酶被证明是筛选实验中最有效的生物催化剂，显示出对（R）-对映异构体的高度对映异构性。用乙酸异丙烯酯代替丙酸乙烯酯会降低所有脂肪酶催化的（E）-4-（苯并[ d]] [1'，3']二氧杂环戊烯-5'-基） -丁-3-烯-2-醇，但在CAL-B和Amano脂肪酶PS的两种制剂的情况下，对映选择率为显著增强（Ë > 100）。在（的制备规模反应ë）-4-（2'，5'-二甲基苯基） -丁-3-烯-2-醇与丙酸乙烯酯催化由CAL-B，未反应的（ - ） - （小号） -醇（EE = 98％）和（+）

  DOI：

  10.1016/j.tetasy.2015.05.006

文献信息

• Copper-catalyzed allylic difluoromethylation of allyl carbonates with (difluoromethyl)zinc reagent
  作者：Kohsuke Aikawa、Koki Ishii、Yu Endo、Koichi Mikami

  DOI：10.1016/j.jfluchem.2017.07.018

  日期：2017.11

  The catalytic allylic difluoromethylation of allyl carbonates with (difluoromethyl)zinc reagent, which can be readily prepared via iodine-zinc exchange reaction of difluoroiodomethane with diethylzinc, was achieved by employing copper salt as a catalyst. The difluoromethylation proceeded with not only good-to-high yields but also complete regioselectivity. Furthermore, the reaction was demonstrated

  通过使用铜盐作为催化剂，通过（二氟甲基）锌试剂可以容易地通过二氟碘甲烷与二乙基锌的碘-锌交换反应制备碳酸烯丙酯的烯丙基二氟甲基化催化。二氟甲基化不仅以良好至高收率进行，而且具有完全的区域选择性。此外，已证明该反应是立体特异性的，因此可以通过处理手性底物获得手性烯丙基二氟甲基化的化合物，所述手性底物是通过α，β-不饱和羰基化合物的催化不对称氢化而合成的。
• Gold- and silver-catalyzed allylic alkylation of 1,3-dicarbonyl compounds with allylic alcohols
  作者：Prasath Kothandaraman、Weidong Rao、Xiaoxiang Zhang、Philip Wai Hong Chan

  DOI：10.1016/j.tet.2008.11.102

  日期：2009.2

  A highly efficient gold- and silver-catalyzed allylic alkylation of 1,3-dicarbonyl compounds with allylic alcohols has been developed. The reaction was shown to proceed expediently for a wide variety of 1,3-dicarbonyl compounds and allylic alcohols, including 1° and terminal ones, under very mild conditions at room temperature in good to excellent yields (55–96%).

  已经开发了用烯丙基醇的高效金和银催化的1，3-二羰基化合物的烯丙基烷基化。在室温下，在非常温和的条件下，反应对多种1,3-二羰基化合物和烯丙醇（包括1°和端基）都可以方便地进行，并且产率高（55-96％）。
• Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity
  作者：ANDRZEJ SKROBISZEWSKI、WITOLD GŁADKOWSKI、PAULINA WALCZAK、ANNA GLISZCZYŃSKA、GABRIELA MACIEJEWSKA、TOMASZ KLEJDYSZ、JAN NAWROT、CZESŁAW WAWRZEŃCZYK

  DOI：10.1007/s12039-015-0823-0

  日期：2015.4

  Eighteen racemic β-aryl-γ-lactones derived from simple aromatic aldehydes have been obtained in the chemical synthesis. Iodolactones (5c and 6c) were synthesized from (E)-4-(benzo[d][1′,3′]-dioxol-5′-yl)-but-3-en-2-one (1). Reductive dehalogenation of iodolactones 5a–c and 6a–c afforded γ-ethyl-γ-lactones (7a–c, 8a–c) whereas the unsaturated lactones (9a–c, 10a–c) were obtained by dehydrohalogenation of iodolactones. All synthesized lactones were fully characterized by spectroscopic data (NMR, IR, HRMS) and subjected to the tests on the antifeedant activity towards Tribolium confusum, Trogoderma granarium and Sitophilus granaries as well to the tests on the antifungal activity towards four Fusarium species. The biological tests allowed to find some relationships between the structure and biological activity of the compounds studied. γ-Ethyl- γ-lactones 7a–c, 8a–c and unsaturated lactones 9a–c, 10a-c were usually stronger antifeedants than their parent iodolactones 5a–c and 6a–c. trans-Iodolactones 6a–c were more active than cis isomers 5a-c both in antifeedant and antifungal assays. The structure of aromatic substituent was the key factor in antifungal activity. The lactones with benzo [d][1,3]dioxole ring (5c, 6c, 7c, 8c, 9c) were the most active whereas those with unsubstituted benzene ring exhibited almost no activity.

  通过化学合成获得了 18 个由简单芳香醛衍生的外消旋 β-芳基-γ-内酯。碘内酯（5c 和 6c）由 (E)-4-(benzo[d][1′,3′]-dioxol-5′-yl)-but-3-en-2-one (1) 合成。碘内酯 5a-c 和 6a-c 的还原脱卤反应得到了 γ-乙基-γ-内酯（7a-c、8a-c），而不饱和内酯（9a-c、10a-c）则是通过碘内酯的脱氢脱卤反应得到的。通过光谱数据（核磁共振、红外光谱、高分辨质谱）对所有合成的内酯进行了全面的表征，并对其进行了测试，以检验其对蒺藜（Tribolium confusum）、谷斑皮蠹（Trogoderma granarium）和谷斑皮蠹（Sitophilus granaries）的杀虫活性，以及对四种镰刀菌（Fusarium）的抗真菌活性。γ-乙基-γ-内酯 7a-c、8a-c 和不饱和内酯 9a-c、10a-c 通常比它们的母体碘内酯 5a-c 和 6a-c 具有更强的杀灭作用。芳香取代基的结构是影响抗真菌活性的关键因素。具有苯并[d][1,3]二恶茂环的内酯（5c、6c、7c、8c、9c）活性最强，而具有未取代苯环的内酯几乎没有活性。
• Prasad, Aviraboina Siva; Satyanarayana, Bollikonda, Asian Journal of Chemistry, 2012, vol. 24, # 12, p. 5503 - 5506,4
  作者：Prasad, Aviraboina Siva、Satyanarayana, Bollikonda

  DOI：——

  日期：——
• Iodine-catalyzed allylation of 1,3-dicarbonyl compounds with allylic alcohols at room temperature
  作者：Weidong Rao、Adeline Hui Ling Tay、Pei Jing Goh、Jessica Mun Ling Choy、Justin Kaijie Ke、Philip Wai Hong Chan

  DOI：10.1016/j.tetlet.2007.11.005

  日期：2008.1

  A highly efficient iodine-catalyzed allylation of 1,3-dicarbonyl compounds with a wide variety of allylic alcohols has been developed. The reaction is operationally straightforward and proceeds under very mild conditions at room temperature in good to excellent yields (up to 99%) and regioselectivity. (c) 2007 Elsevier Ltd. All rights reserved.