3,4-二氢-2,2-二甲基-2H-萘并[1,2-b]吡喃 | 16274-33-2

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 中文名称: 3,4-二氢-2,2-二甲基-2H-萘并[1,2-b]吡喃
• 中文别名: 3,4-二氢-2,2-二甲基-2H-萘并[1,2-B]吡喃
• 英文名称: 2,2-dimethyl-3,4-dihydro-2H-benzl[h]chromene
• 英文别名: 3,4-Dihydro-2,2-dimethylnaphtho[1,2-b]pyran；3,4-dihydro-2,2-dimethyl-2H-naphtho[1,2-b]-pyran；2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene；2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromen；3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran；2,2-dimethyl-3,4-dihydrobenzo[h]chromene
• CAS: 16274-33-2
• 化学式: C₁₅H₁₆O
• mdl: MFCD19441054
• 分子量: 212.291
• InChiKey: HYUYQZUDUFSJRS-UHFFFAOYSA-N

物化性质

• 沸点：
  334.7±12.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2902909090
• 储存条件：
  2-8℃，请密封保存，并置于干燥处。

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2,2-二甲基-2H-萘并[1,2-b]吡喃 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 40.0h， 以0.07 g的产率得到2,2-dimethyl-2H-benzo[h]chromene
  参考文献：
  名称：

  Ahluwalia, V. K.; Hira, P. K.; Jolly, R. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 10, p. 961 - 962

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-2,2-二甲基-2H-萘并[1,2-B]吡喃-5,6-二酮 在 磷化氢 、 氢碘酸 作用下， 生成 3,4-二氢-2,2-二甲基-2H-萘并[1,2-b]吡喃
  参考文献：
  名称：

  Hooker, Journal of the Chemical Society, 1896, vol. 69, p. 1365

  摘要：

  DOI：

文献信息

• Reusable Scandium/Ionic Liquid Catalyst System for Sequential C-C and C-O Bond Formations between Phenols and Dienes with Atom Economy
  作者：So Youn

  DOI：10.1055/s-2007-990963

  日期：2007.12

  Mild, efficient, and atom economical sequential C-C/C-O bond formations between phenols and dienes using the reusable catalyst system, Sc(OTf) 3 -[bmim][PF 6 ], have been developed to afford in good yields a variety of dihydrobenzopyran and dihydrobenzofuran ring systems, which are important motifs in both naturally occurring and biologically active compounds. In these reactions the ionic liquid acts

  使用可重复使用的催化剂体系 Sc(OTf) 3 -[bmim][PF 6 ] 在苯酚和二烯之间形成温和、高效且原子经济的连续 CC/CO 键，已开发出高产率的各种二氢苯并吡喃和二氢苯并呋喃环系统，它们是天然存在和生物活性化合物中的重要基序。在这些反应中，离子液体不仅充当有效的添加剂，而且充当促进催化剂回收的固定剂。
• Catalytic Tandem and One-Pot Dehydrogenation–Alkylation and −Insertion Reactions of Saturated Hydrocarbons with Alcohols and Alkenes
  作者：Junghwa Kim、Nuwan Pannilawithana、Chae S. Yi

  DOI：10.1021/acscatal.6b02186

  日期：2016.12.2

  reaction of saturated hydrocarbon substrates with alcohols to form the alkyl-substituted alkene and arene products. The analogous one-pot dehydrogenation–insertion of saturated ketones with alkenes and dienes directly yielded synthetically useful 2-alkylphenol and benzopyran products in a highly regio- and stereoselective manner without forming any wasteful byproducts.

  氢化钌催化剂已成功用于饱和烃底物与醇的串联sp 3 C–H脱氢-烷基化反应，形成烷基取代的烯烃和芳烃产品。饱和酮与烯烃和二烯的类似的一锅脱氢插入反应，可以以高度区域选择性和立体选择性的方式直接产生合成上有用的2-烷基苯酚和苯并吡喃产物，而不会形成任何浪费的副产物。
• Synthesis and vasorelaxant activity of 4-(cyclic amido)-2H-naphtho[1,2-b]pyrans
  作者：Wen-Fei Chiou、Shyh-Yuan Li、Li-Kang Ho、Ming-Ling Hsien、Ming-Jaw Don

  DOI：10.1016/s0223-5234(01)01273-9

  日期：2002.1

  A series of 4-(cyclic amido)-2H-naphtho[1,2-b]pyrans related to cromakalim (1) has been prepared and their vasorelaxant activities on isolated rat thoracic aorta precontracted with phenylephrine have been evaluated. The relaxant mechanism of 3a was found not through ATP-sensitive K(+) channels as cromakalim, but through opening voltage-sensitive K(+) channels.

  制备了一系列与cromakalim（1）相关的4-（环状酰胺基）-2H-萘并[1,2-b]吡喃，并评估了它们对苯肾上腺素预收缩的离体大鼠胸主动脉的血管舒张活性。发现3a的弛豫机理不是通过ATP敏感的K（+）通道作为cromakalim，而是通过打开电压敏感的K（+）通道。
• The total synthesis of β-lapachone
  作者：Aná Claudia F. Amaral、Roderick A. Barnes

  DOI：10.1002/jhet.5570290614

  日期：1992.10

  The synthesis of β-lapachone has been accomplished in eight steps with an overall yield of twenty-three percent starting from alpha-naphthol. The yields from the various steps were sufficiently good to insure that the derivatives of β-lapachone which might be effective against Chagas' disease could be obtained in reasonable amounts.

  β-拉帕酮的合成已从8个步骤完成，从α-萘酚开始的总产率为23％。来自各个步骤的产率足够好以确保可以合理量获得可能有效对抗恰加斯氏病的β-拉帕酮衍生物。
• Convenient Syntheses of Naturally Occurring Angular and Linear Naphthopyrans†
  作者：Madhusudan V. Paradkar、Himanshu M. Godbole、Anup A. Ranade、Augustine R. Joseph

  DOI：10.1039/a708718g

  日期：——

  A convenient synthesis of naturally occurring angular naphthopyrans and their 6-demethoxy derivatives is described starting from 2-acetyl-1-naphthols along with the synthesis of linear naphthopyrans from 3-acetyl-2-naphthol.

  描述了从 2-乙酰基-1-萘酚以及从 3-乙酰基-2-萘酚合成线性萘并吡喃的天然存在的有角萘并吡喃及其 6-脱甲氧基衍生物的方便合成。