4-茚满甲醛 | 51932-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 4-茚满甲醛
• 中文别名: (9ci)-2,3-二氢-1H-茚-4-羧醛
• 英文名称: indane-4-carboxaldehyde
• 英文别名: indan-4-carbaldehyde；Indan-4-carbaldehyd；4-indanaldehyde；4-formylindane；2,3-dihydro-1H-indene-4-carbaldehyde
• CAS: 51932-70-8
• 化学式: C₁₀H₁₀O
• mdl: MFCD18808942
• 分子量: 146.189
• InChiKey: VAZZQRFSDNZKPO-UHFFFAOYSA-N

物化性质

• 沸点：
  136 °C(Press: 24 Torr)
• 密度：
  1.122±0.06 g/cm3(Predicted)
• 保留指数：
  1307

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2912299000
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  4-茚满甲醛 在 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 乙醚 、 苯 为溶剂， 反应 24.0h， 生成 4-(3-bromopropyl)-2,3-dihydro-1H-indene
  参考文献：
  名称：

  Isabelle, M. Elaine; Wightman, Robert H.; Avdovich, Hajro W., Canadian Journal of Chemistry, 1980, vol. 58, p. 1344 - 1349

  摘要：

  DOI：
• 作为产物：
  描述：

  茚满 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hypobromide 、 pyridinium chlorochromate 作用下， 以 1,4-二氧六环 、 四氯化碳 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 107.0h， 生成 4-茚满甲醛
  参考文献：
  名称：

  Aromatische Spirane, 22. Mitt.: Darstellung von Cyclopenteno-4,5-indan-1-on und 2-Carboxymethyl-bzw. 4-Chlormethyl-indan als Synthone f�r Synthesen von anellierten 2,2?-Spirobiindanonen

  摘要：

  The title compounds were prepared as follows: tert.-butyl-indane (10) was formylated to give a 72:28 mixture of the aldehydes 23a and 23b which were submitted to a Knoevenagel-Doebner condensation to afford the cinnamonic acids 24. From the mixture, the pure stereoisomer 24a was obtained by one crystallization in 57% yield. Its methylester 27a could be quantitatively dealkylated to the methylester 8 by treatment with AlCl3 in toluene. Cyclization to the indanone 9 was then performed via the propionic acid 7 with polyphosphoric acid in 95% yield. From 9 the carboxymethyl derivative 30 was obtained by treatment with dimethylcarbonate and NaH. The second synthone 4-chlormethylindane (19) was prepared from the corresponding alcohol 18 (in 82% yield) which in turn could be obtained from methylester 17 by reduction with LiAlH4. The latter was accessible in 75% yield by dealkylation of ester 13.

  DOI：

  10.1007/bf00813793

文献信息

• Addition of Carbon Nucleophiles to Tricarbonylchromium Complexes of 1,2-Dihydrocyclobutabenzene, Indane, 1,2,3,4-Tetrahydronaphtbalene and<i>ortho</i>-Xylene
  作者：E. Peter Kündig、Chantal Grivet、Eric Wenger、Gerald Bérnardinelli、Alan F. Williams

  DOI：10.1002/hlca.19910740836

  日期：1991.12.11

  of products. In several cases, the mixtures of the intermediate anionic cyclohexadienyl complexes can be equilibrated to give, after oxidation, β-substituted derivatives of 1,2,3,4-tetrahydronaphthalene and ortho-xylene selectively. EHMO calculations were carried out, and they rationalize the observed α-regioselectivity of nucleophilic addition under kinetic control, The X-ray structures of 1 and 4

  3-取代的1,2-二氢环丁苯（双环[4. 2. 0]八-1,3,5-三烯）很容易从[Cr（CO）3（1,2-二氢环丁苯）]（1）中通过两步序列，涉及亲核试剂的添加和中间体阴离子环己二烯基复合物的氧化。使用的亲核试剂包括LiCMe 2 CN（A），LiCH 2 CN（B），LiC（Me）（OR）CN（C），（D），（E），LiCMe 2 CO 2 Me（F）和LiCH 2 CO 2（t-Bu）（G）。[Cr（CO）3（茚满）]（2）也具有高度区域选择性反应，产生α-取代，而[Cr（CO）3（四氢萘）]（3）和[Cr（CO）3（邻二甲苯）]（4）得到产物的混合物。在几种情况下，可以平衡中间体阴离子环己二烯基络合物的混合物，以在氧化后选择性地得到1,2,3,4-四氢萘和邻二甲苯的β-取代衍生物。进行了EHMO计算，合理化了动力学控制下亲核加成反应的α-区域选择性。报道了1和4的X射线结构，两种化
• Synthesis of aromatic aldehydes by organocatalytic [4+2] and [3+3] cycloaddition of α,β-unsaturated aldehydes
  作者：Bor-Cherng Hong、Hsing-Chang Tseng、Shang-Hung Chen

  DOI：10.1016/j.tet.2007.01.039

  日期：2007.3

  Organocatalytic inter- and intramolecular [4+2] and [3+3] cycloadditions of α,β-unsaturated aldehydes to give polysubstituted aromatic aldehydes are described. High periselectivity for the cycloadditions, with catalyst effects exerted by l-proline and pyrrolidine–HOAc, as well as cocatalyst, additive effects, has been observed.

  描述了α，β-不饱和醛的有机催化的分子间和分子内[4 + 2]和[3 + 3]环加成以得到多取代的芳族醛。观察到对环加成反应的高选择性是由l-脯氨酸和吡咯烷-HOAc产生的催化剂作用，以及助催化剂的加成作用。
• Aralkyl-tetrahydro-pyridines, their preparation and pharmaceutical compositions containing same
  申请人：Baroni Marco

  公开号：US20050014795A1

  公开（公告）日：2005-01-20

  The present invention relates to compounds of formula (I): in which X represents N or CH; R 1 represents a hydrogen or halogen atom or a CF 3 group; n is an integer from 1 to 5; A represents a partially saturated carbonaceous bi- or tricycle; it also relates to their salts, solvates, N-oxides, the pharmaceutical compositions containing them, a method for their preparation and synthesis intermediates in this method.

  这项发明涉及以下式(I)的化合物： 其中 X代表N或CH；R1代表氢原子或卤素原子或CF3基团；n是1到5之间的整数；A代表部分饱和的碳质双环或三环；还涉及它们的盐、溶剂合物、N-氧化物、含有它们的药物组合物、其制备方法以及该方法中的合成中间体。
• Synthesis and biological evaluation of aminothiazoles against Histoplasma capsulatum and Cryptococcus neoformans
  作者：Keisuke Ishita、Stavros Stefanopoulos、Ahmed Khalil、Xiaolin Cheng、Werner Tjarks、Chad A. Rappleye

  DOI：10.1016/j.bmc.2018.01.024

  日期：2018.5

  group, the thiazole core, and the methylene linker between these two structural elements. In general, compounds with lipophilic [5+6] bicyclic ring systems, such as the 7-benzothiophenyl- and 4-indanyl groups, at the 5-position were 2–3 times more active against both fungal species as compared to 41F5. Also, introduction of a carbonyl group at the methylene linker of 41F5 resulted in a 2–3-fold increase

  描述了四十种新型 2-氨基唑类似物库的设计和合成，以及它们作为抗荚膜组织胞浆菌和新型隐球菌的抗真菌化合物的评估。这些结构源自N -[5-(1-萘基甲基)-2-噻唑基]环己烷甲酰胺 (41F5)，这是一种先前通过表型筛选鉴定的抑真菌剂（ Antimicrob Agents Chemother. 2013；57:4349）。提高 41F5 效力和水溶性的修饰主要集中在 5-萘基、噻唑核心以及这两个结构元件之间的亚甲基连接基。一般来说，5 位具有亲脂性 [5+6] 双环系统（例如 7-苯并噻吩基和 4-茚满基）的化合物对两种真菌的活性比 41F5 高 2-3 倍。此外，在 41F5 的亚甲基连接基上引入羰基导致效力增加 2-3 倍。这些高活性化合物还对鼠 P388D1 巨噬细胞表现出较低的毒性，导致选择性指数范围为 63 至 >200。对氟康唑敏感的新型隐球菌菌株具有高度活性的化合物对这种真菌的氟康唑抗性变种具有几乎相同的活性，表明
• CBI analogues of the duocarmycins and CC-1065
  申请人：Boger L. Dale

  公开号：US20050026987A1

  公开（公告）日：2005-02-03

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≧1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC 50 =2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp 2 , sp 3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.

  一系列广泛的CBI类似物，包括二聚卡蜜素和CC-1065的类似物，探索了第一个吲哚DNA结合亚基中取代基效应的细节。一般来说，在吲哚C5位置的取代导致细胞毒性增强，可以达到≧1000倍，提供了更强效（IC50=2-3 pM）的含有单个DNA结合亚基的简化类似物，比CBI-TMI、二聚卡蜜素SA或CC-1065更有效。细胞毒性增加与DNA烷基化速率和效率的增加密切相关。与基于DSA或CPI的类似物相比，这种效应在CBI类似物中更为显著。此外，这种效应对于C5取代基的电子性质不太敏感，但对于取代基的大小、刚性长度和形状（sp、sp2、sp3杂化）敏感，这与预期一致，即这种影响仅仅是由于其存在。