dimethyl indan-5,6-dicarboxylate | 56598-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: dimethyl indan-5,6-dicarboxylate
• 英文别名: indan-5,6-dicarboxylic acid dimethyl ester；Indan-5,6-dicarbonsaeure-dimethylester；5,6-Bis-(methoxycarbonyl)-indan；5,6-Dicarbomethoxyindan；dimethyl 2,3-dihydro-1H-indene-5,6-dicarboxylate
• CAS: 56598-67-5
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: DOSPHYWSMGIUBB-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• 沸点：
  175 °C(Press: 3 Torr)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl indan-5,6-dicarboxylate 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 以50%的产率得到(6-Hydroxymethyl-indan-5-yl)-methanol
  参考文献：
  名称：

  Differential Reactivity Pattern of Hybrid o-Quinodimethane Precursors: Strategic Expansion to Annulated Benzocycloalkanes via Rongalite

  摘要：

  A hybrid benzocyclobutene (BCB) molecular frames embedding sultine or sulfone moiety has been synthesized via utilization of rongalite. The selective Diels-Alder reaction has been realized at sultine or sulfone terminus in the hybrid BCB system to prepare functionalized BCB molecular frames. The methodology has been generalized for assembling various benzocycloalkanes containing a sultine unit and the strategy has been expanded to generate various annulated benzocycloalkanes.

  DOI：

  10.1021/jo900658z
• 作为产物：
  描述：

  methyl 3-(E)-<5-<2-(E)-methoxycarbonylethenyl>-6-oxabicyclo<3.1.0>hex-1-yl>acrylate 在 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 70.0 ℃ 、999.99 MPa 条件下， 反应 72.0h， 以82%的产率得到dimethyl indan-5,6-dicarboxylate
  参考文献：
  名称：

  Versatile Synthesis of 11-Oxabicyclo[4.4.1]undeca-1,5-dienes by Selective Epoxidation of 1,6-Disubstituted (E,Z,E)-1,3,5-Hexatrienes and Subsequent Cope Rearrangement

  摘要：

  1,6-Disubstituted (E,Z,E)-1,3,5-hexatrienes (1a-c, 2a-e), obtained in good yields (43-81%) by 2-fold Heck couplings of 1,2-dibromocyclopentene and 1,2-dibromocyclohexene, respectively, with alkenes, can be oxidized regioselectively at the central double bond with various oxidants such as dimethyldioxirane (DMDO), m-CPBA, or trifluoroperacetic acid in moderate to good yields (45-87%). The resulting 1,2-dialkenylcyclohexene epoxides 4a-e undergo thermal Cope rearrangements to furnish 1,6-oxygen-bridged cyclodeca-1,5-dienes 8a-e, which are 2-fold anti-Bredt bridgehead alkenes. The structure of compound 8a was established by X-ray analysis. The corresponding 1,2dialkenylcyclopentene epoxides 3a-c give only 2,2-dialkenylcyclopentanones 9a,b by an acid-catalyzed 1,2-alkenyl shift (71-100% yield) or indan derivatives 12b,c (46-82%) resulting from elimination, 6 pi-electrocyclization, and aromatization.

  DOI：

  10.1021/jo981496u

文献信息

• Rhodium-catalyzed convenient synthesis of functionalized tetrahydronaphthalenes
  作者：Ken Tanaka、Yayoi Sawada、Yusuke Aida、Maliny Thammathevo、Rie Tanaka、Hiromi Sagae、Yousuke Otake

  DOI：10.1016/j.tet.2009.12.042

  日期：2010.2

  studies indicated that the present rhodium-catalyzed [2+2+2] cycloaddition proceeds through the rhodacyclopentadiene intermediate generated by oxidative coupling of a diyne with rhodium. On the other hand, in the reactions of diynes and dimethyl acetylenedicarboxylate, the rhodacyclopentadiene intermediate generated by oxidative coupling of a diyne and a monoyne with rhodium would also be involved

  阳离子铑（I）/ H 8在温和的反应条件下已经完成了功能化四氢萘的便捷合成和聚合反应-BINAP配合物与功能化单炔的1,2-辛二炔衍生物的[2 + 2 + 2]环加成反应。研究了二炔系链长度的影响，结果表明1,6-庚二炔和1,7-辛二炔的反应性高于1,8-壬二炔。机理研究表明，目前的铑催化的[2 + 2 + 2]环加成反应是通过二炔与铑的氧化偶联生成的Rhodacyclopentadiene中间体进行的。另一方面，在二炔和乙炔二甲酸二甲酯的反应中，还涉及由二炔和单炔与铑的氧化偶联产生的若丹环戊二烯中间体。
• Palladium-catalyzed aromatization of β-bromovinyl aldehydes with alkenes
  作者：Chan Sik Cho、Daksha B. Patel、Sang Chul Shim

  DOI：10.1016/j.tet.2005.08.001

  日期：2005.10

  β-Bromovinyl aldehydes, which are readily available from ketones and PBr3/DMF/CHCl3, are aromatized with suitably electron withdrawing group substituted alkenes in THF at 125 °C in the presence of a catalytic amount of a palladium catalyst along with a base.

  容易从酮和PBr 3 / DMF / CHCl 3中获得的β-溴乙烯基醛在催化量的钯催化剂和碱存在下，在125°C下用适当的吸电子基团取代的烯烃在THF中芳构化。
• Skeletal Transformation of Unactivated Arenes Enabled by a Low-Temperature Dearomative (3 + 2) Cycloaddition
  作者：Sajan Pradhan、Fahimeh Mohammadi、Jean Bouffard

  DOI：10.1021/jacs.3c02314

  日期：2023.6.7

  exchange of the ring carbons: a two-carbon fragment from the original aromatic ring is replaced with another from the incoming dienophile, introducing an unconventional disconnection for the synthesis of ubiquitous aromatic building blocks. Applications of this two-step sequence to the preparation of substituted acenes, isotopically labeled molecules, and medicinally relevant compounds are demonstrated

  像苯这样的简单芳香族化合物是丰富的原料，其衍生物的制备主要从亲电取代反应开始，或者较少见的是还原反应。它们的高稳定性使它们特别不愿意在普通反应条件下参与环加成反应。在这里，我们展示了 1,3-diaza-2-azoniaallene 阳离子在室温下与未活化的苯衍生物进行形式 (3 + 2) 环加成的特殊能力，提供了多克级的热稳定脱芳构化加合物。容忍极性官能团的环加成激活环以进一步细化。在用亲二烯体处理时，环加合物会经历 (4 + 2) 环加成-环逆转级联反应，产生取代或稠合的芳烃，包括萘衍生物。整个序列通过环碳的交换导致芳烃的转化：来自原始芳环的双碳片段被来自进入的亲双烯体的另一个取代，为普遍存在的芳香结构单元的合成引入非常规的断开。证明了该两步序列在制备取代并苯、同位素标记分子和医学相关化合物中的应用。
• Reactivity of Electron-Deficient Alkynes on Gold Nanoparticles
  作者：Antonio Leyva-Pérez、Judit Oliver-Meseguer、Jose R. Cabrero-Antonino、Paula Rubio-Marqués、Pedro Serna、Saud I. Al-Resayes、Avelino Corma

  DOI：10.1021/cs400362c

  日期：2013.8.2

  Propiolates cyclotrimerize in the presence of catalytic amounts of gold nanoparticles to give aryl benzoates in high yields and with turnover frequencies of thousands per hour. Types of alkynes other than propiolates do not react, and, if molecular oxygen is present and dissociated by the gold nanoparticles, electron-rich arenes engage with the propiolate to form a new C-C bond. The activation of propiolates and electron-rich arenes to form C-C bonds, beyond gold-catalyzed Michael additions, constitutes a new example of how and where gold nanoparticles modify the electronic density of unsaturated C-C bonds and opens the door to future transformations.
• Alder et al., Justus Liebigs Annalen der Chemie, 1959, vol. 627, p. 59,72
  作者：Alder et al.

  DOI：——

  日期：——