4-chloro-1,3-dihydroisobenzofuran | 1013915-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 4-chloro-1,3-dihydroisobenzofuran
• 英文别名: 4-Chloro-1,3-dihydro-isobenzofuran；4-chloro-1,3-dihydro-2-benzofuran
• CAS: 1013915-44-0
• 化学式: C₈H₇ClO
• 分子量: 154.596
• InChiKey: GJTHGXJJBGDIHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-chloro-1,3-dihydroisobenzofuran 、 苯甲醛 在 4,4'-二叔丁基苯并 、 lithium 、 水 作用下， 以 四氢呋喃 为溶剂， 以28%的产率得到4-(1-hydroxylphenylmethyl)phthalan
  参考文献：
  名称：

  Selective Lithiation of 4- and 5-Halophthalans

  摘要：

  The reaction of 4- and 5-halophthalans 5 with lithium and a catalytic amount of DTBB at -78 degrees C leads to the formation of the corresponding functionalized organolithium intermediates 6 and 11, which by reaction with carbonyl compounds give, after hydrolysis, the expected substituted phthalans 8 and 13, respectively. When after reaction with the carbonyl compound the system is allowed to react at 0 degrees C, a second lithiation occur: A reductive opening of the heterocycle takes place with some regioselectivity leading to new organolithium intermediates 9 and 14/15 that by reaction with electrophiles lead, after hydrolysis, to polyfunctionalized molecules 10 and 16/17, respectively.

  DOI：

  10.3987/com-08-s(f)85
• 作为产物：
  描述：

  3-chlorophthalaldehyde 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-chloro-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  Selective Lithiation of 4- and 5-Halophthalans

  摘要：

  The reaction of 4- and 5-halophthalans 5 with lithium and a catalytic amount of DTBB at -78 degrees C leads to the formation of the corresponding functionalized organolithium intermediates 6 and 11, which by reaction with carbonyl compounds give, after hydrolysis, the expected substituted phthalans 8 and 13, respectively. When after reaction with the carbonyl compound the system is allowed to react at 0 degrees C, a second lithiation occur: A reductive opening of the heterocycle takes place with some regioselectivity leading to new organolithium intermediates 9 and 14/15 that by reaction with electrophiles lead, after hydrolysis, to polyfunctionalized molecules 10 and 16/17, respectively.

  DOI：

  10.3987/com-08-s(f)85

文献信息

• Assessment of the regioselectivity in the condensation reaction of unsymmetrical o -phthaldialdehydes with alanine
  作者：Agathe C.A. D'Hollander、Nicholas J. Westwood

  DOI：10.1016/j.tet.2017.11.035

  日期：2018.1

  context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale

  合成异吲哚啉酮（一种特权的生物活性杂环核心结构）的一种方法涉及邻苯二甲醛与合适的含氮亲核试剂的缩合反应。在使用在芳环中包含其他取代基的邻苯二甲醛的背景下，重新审视了这一迷人的反应，从而对该反应的区域选择性进行了详细分析。十一个单取代的邻位合成了苯二醛并与丙氨酸反应。跨十一个底物观察到的区域选择性导致设计了在非常高的控制下反应的双取代底物。克级反应，然后酯化，以高收率得到了一种主要的区域异构体。此外，在两种新型单氘代底物反应时观察到的区域选择性导致对机理的了解增加。
• A g-C₃N₄-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C–H oxygenations
  作者：Pengxin Geng、Yurong Tang、Guanglong Pan、Wentao Wang、Jinchuan Hu、Yunfei Cai

  DOI：10.1039/c9gc02870f

  日期：——

  A metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C–H oxygenations using oxygen as an oxidant. This visible light mediated oxidation reaction utilizes graphitic carbon nitride (g-C3N4) as a recyclable, nontoxic and low cost photocatalyst. Mild reaction conditions allow for the generation of synthetically and biologically valued isochromannones, phthalides

  已开发出一种无金属的非均相光催化系统，用于使用氧气作为氧化剂的高效苄基CH氧化。这种可见光介导的氧化反应利用石墨碳氮化物（gC 3 N 4）作为可回收，无毒且低成本的光催化剂。温和的反应条件可从易于获得的烷基芳族前体中以高收率生成合成和生物学上有价值的异苯并二氢醌，邻苯二甲酸，异喹啉酮，异吲哚啉酮和氧杂蒽。gC 3 N 4的异质性催化系统可轻松回收和循环利用，并可多次使用而不会损失活性。通过在生物活性和具有药物价值的靶标合成中的应用，进一步证明了这种“绿色”方法的综合效用。
• FLUOROBORON COMPOUND HAVING AROMATIC RING OR SALT THEREOF, AND METHOD FOR PRODUCING COMPOUND HAVING CYCLIC ETHER-FUSED AROMATIC RING USING THE SAME
  申请人：Tanaka Keigo

  公开号：US20100056788A1

  公开（公告）日：2010-03-04

  Provided is a fluoroboron compound which is highly safe and stable and is capable of forming a cyclic ether-fused ring by the intramolecular alkoxymethylation reaction, or a salt thereof. The compound can be synthesized by the intramolecular alkoxymethylation reaction of a fluoroboron compound represented by the formula (I) or a salt thereof in the presence of a metal catalyst. (wherein the moiety represented by the formula represents an aromatic ring; L represents a substituent such as a halogen atom; R represents a substituted or unsubstituted alkylene group having 1 or 2 carbon atoms; and M represents an alkali metal cation or the like, with the proviso that L and —R—OCH 2 BF 3 M are respectively located on contiguous carbon atoms on the aromatic ring, or in the case of a fused aromatic ring, on two carbon atoms adjacent to one carbon at the fused position).

  提供的是一种高度安全和稳定的氟硼化合物，能够通过分子内烷氧甲基化反应形成环状醚融合环，或其盐。该化合物可以在金属催化剂存在下，通过公式（I）表示的氟硼化合物或其盐的分子内烷氧甲基化反应合成。（其中由公式表示的基团代表芳香环；L代表取代基，如卤素原子；R代表取代或未取代的1或2个碳原子的烷基；M代表碱金属阳离子等，条件是L和-R-OCH2BF3M分别位于相邻的芳香环碳原子上，或在融合芳香环的情况下，在相邻的两个碳原子上，且其中一个碳原子在融合位置上）。
• Fluoroboron compound having aromatic ring or salt thereof, and method for producing compound having cyclic ether-fused aromatic ring using the same
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US08273885B2

  公开（公告）日：2012-09-25

  Provided is a fluoroboron compound which is highly safe and stable and is capable of forming a cyclic ether-fused ring by the intramolecular alkoxymethylation reaction, or a salt thereof. The compound can be synthesized by the intramolecular alkoxymethylation reaction of a fluoroboron compound represented by the formula (I) or a salt thereof in the presence of a metal catalyst. (wherein the moiety represented by the formula represents an aromatic ring; L represents a substituent such as a halogen atom; R represents a substituted or unsubstituted alkylene group having 1 or 2 carbon atoms; and M represents an alkali metal cation or the like, with the proviso that L and —R—OCH2BF3M are respectively located on contiguous carbon atoms on the aromatic ring, or in the case of a fused aromatic ring, on two carbon atoms adjacent to one carbon at the fused position).

  提供了一种高度安全稳定的氟硼化合物，能够通过分子内烷氧甲基化反应形成环状醚融合环，或其盐。该化合物可以在金属催化剂存在下，通过式(I)或其盐所代表的氟硼化合物的分子内烷氧甲基化反应合成。（其中，由式所代表的基团表示芳香环；L表示卤素原子等取代基；R表示具有1或2个碳原子的取代或未取代的烷基；M表示碱金属阳离子等，但须满足L和—R—OCH2BF3M分别位于芳香环上相邻的碳原子上，或者在融合芳香环的情况下，在相邻的两个碳原子上位于一个碳原子上）。
• FLUOROBORON COMPOUND HAVING AROMATIC RING OR SALT THEREOF, AND PROCESS FOR PRODUCTION OF COMPOUND HAVING CYCLIC ETHER-FUSED AROMATIC RING BY USING THE SAME
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP2062901A1

  公开（公告）日：2009-05-27

  Provided is a fluoroboron compound which is highly safe and stable and is capable of forming a cyclic ether-fused ring by the intramolecular alkoxymethylation reaction, or a salt thereof. The compound can be synthesized by the intramolecular alkoxymethylation reaction of a fluoroboron compound represented by the formula (I) or a salt thereof in the presence of a metal catalyst. (wherein the moiety represented by the formula represents an aromatic ring; L represents a substituent such as a halogen atom; R represents a substituted or unsubstituted alkylene group having 1 or 2 carbon atoms; and M represents an alkali metal cation or the like, with the proviso that L and -R-OCH2BF3M are respectively located on contiguous carbon atoms on the aromatic ring, or in the case of a fused aromatic ring, on two carbon atoms adjacent to one carbon at the fused position).

  本发明提供了一种通过分子内烷氧甲基化反应能够形成环醚融合环的高度安全稳定的氟硼化合物或其盐。该化合物可在金属催化剂存在下，通过式（I）代表的氟硼化合物或其盐的分子内烷氧甲基化反应合成。 (其中由式 代表芳香环；L 代表取代基，如卤素原子；R 代表具有 1 或 2 个碳原子的取代或未取代的亚 烷基；M 代表碱金属阳离子或类似物，但 L 和 -R-OCH2BF3M 分别位于芳香环上相邻的碳原子上，或在芳香环熔合的情况下，位于熔合位 置上相邻一个碳原子的两个碳原子上)。