dimethyl (1R,8S,9S,10S,12R,13R)-11,14-dioxapentacyclo[6.5.1.02,7.09,13.010,12]tetradeca-2,4,6-triene-10,12-dicarboxylate | 234443-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: dimethyl (1R,8S,9S,10S,12R,13R)-11,14-dioxapentacyclo[6.5.1.02,7.09,13.010,12]tetradeca-2,4,6-triene-10,12-dicarboxylate
• CAS: 234443-14-2
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.284
• InChiKey: FJEZPNPGDOESEN-KUGLLBKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1α,4α,4aβ,10aβ,5α,8α,8aβ,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione 、 dimethyl (1R,8S,9S,10S,12R,13R)-11,14-dioxapentacyclo[6.5.1.02,7.09,13.010,12]tetradeca-2,4,6-triene-10,12-dicarboxylate 以48%的产率得到tetramethyl (1R,2S,4R,5S,6R,7R,8R,9R,16S,17S,18S,19S,20R,21S,23R,24S,25R,26R,27R,28R,35S,36S,37S,38S)-3,22-dioxo-40,41,43,44-tetraoxapentadecacyclo[22.14.1.15,20.17,18.19,16.126,37.128,35.02,23.04,21.06,19.08,17.010,15.025,38.027,36.029,34]tetratetraconta-10,12,14,29,31,33-hexaene-7,18,26,37-tetracarboxylate
  参考文献：
  名称：

  Building BLOCK Strategies for the Synthesis of Molecular Clefts with Inside Functionality

  摘要：

  A new general route to U-type cavity structures (molecular clefts) with inside functionality has been developed using wall extension or base/ roof assembly methods which draw upon (i) the 1,3 dipolar cycloaddition reaction between alkenes and cyclobutene epoxides (ACE coupling) or (ii) the Diels-Alder reaction of alkenes with fused dihydropyridazines (s-tetrazine coupling). In this way, functional units (e.g., crown ethers, redox active naphthalenes) have been attached stereospecifically to short-walled bis-alkenes 1-5 to produce cavity structure 6-10 with top of-wall separations (C to C) from 4.5 to 12.7 Angstrom.

  DOI：

  10.1021/ol9905396
• 作为产物：
  描述：

  dimethyl (2aR,3S,8R,8aS)-2a,3,8,8a-tetrahydro-3,8-epoxycyclobuta[b]naphthalene-1,2-dicarboxylate 在 叔丁基过氧化氢 、 甲基锂 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 生成 dimethyl (1R,8S,9S,10S,12R,13R)-11,14-dioxapentacyclo[6.5.1.02,7.09,13.010,12]tetradeca-2,4,6-triene-10,12-dicarboxylate
  参考文献：
  名称：

  顺-Facial杂桥连[ Ñ ] polynorbornanes：一类新的polarofacial框架分子的稠合的7-氧杂-和7- azanorbornanes组成

  摘要：

  新氧桥降冰片烷-稠合环丁烯环氧化物和双- （环丁烯环氧化物）中描述和示出为7-azanorbornenes以产生立体选择性反应顺式-facial Ñ，ö -bridged polynorbornanes和stereorandomly 7-oxanorbornenes以产生ö，ö -桥接polynorbornanes作为混合物顺式-facial和抗-facial产品。1个含有多达六个Polarofacial系统SYN -facial降冰片烷桥描述的，当具有七个共面的氧原子系统已经制备通过将末端环氧环至O 5-[5]聚降冰片烷。酯取代的1,3,4-恶二唑被示出为是有用的试剂，用于耦合7- oxanorbornanes和主要产生顺-facial ö -bridged polarofacial与它们一起系统抗-facial异构体。

  DOI：

  10.1016/s0040-4020(00)01027-9

文献信息

• Incorporation of a Molecular Hinge into Molecular Tweezers by Using Tandem Cycloadditions onto 5,6-Dimethylenenorbornene
  作者：Ronald N. Warrener、Douglas N. Butler、Ligong Liu、Davor Margetic、Richard A. Russell

  DOI：10.1002/1521-3765(20010803)7:15<3406::aid-chem3406>3.0.co;2-m

  日期：2001.8.3

  Site-selective 1.3-dipolar coupling at the norbornene pi -bond of 5,6-dimethylenenorbornene I yields cycloadducts with an end-fused 1.3-diene system which have been reacted with N=N (or C=C) dienophiles to produce ribbon molecules. in which the internal diazacyclohexene (or cyclohexene) subunits are capable of acting as conformational hinges. Direct coupling of 5,6-dimethylene- norbornene with 1.3,4-oxadiazoles or dual coupling with bis(cyclobutene epoxides) afforded bis(1,3-dienes) that diastereoselectively react with dienophiles to produce new. conformationally mobile. molecular tweezers.
• syn-Facial hetero-bridged [n]polynorbornanes: a new class of polarofacial framework molecules composed of fused 7-oxa- and 7-azanorbornanes
  作者：Ronald N. Warrener、Davor Margetic、Patrick J. Foley、Douglas N. Butler、Alain Winling、Kerry A. Beales、Richard A. Russell

  DOI：10.1016/s0040-4020(00)01027-9

  日期：2001.1

  syn-facial N,O-bridged polynorbornanes and stereorandomly with 7-oxanorbornenes to produce O,O-bridged polynorbornanes as mixtures of syn-facial and anti-facial products. 1 Polarofacial systems containing up to six syn-facial norbornane bridges are described, while systems with seven co-facial oxygen atoms have been prepared by incorporating terminal epoxide rings to O5-[5]polynorbornanes. Ester-substituted

  新氧桥降冰片烷-稠合环丁烯环氧化物和双- （环丁烯环氧化物）中描述和示出为7-azanorbornenes以产生立体选择性反应顺式-facial Ñ，ö -bridged polynorbornanes和stereorandomly 7-oxanorbornenes以产生ö，ö -桥接polynorbornanes作为混合物顺式-facial和抗-facial产品。1个含有多达六个Polarofacial系统SYN -facial降冰片烷桥描述的，当具有七个共面的氧原子系统已经制备通过将末端环氧环至O 5-[5]聚降冰片烷。酯取代的1,3,4-恶二唑被示出为是有用的试剂，用于耦合7- oxanorbornanes和主要产生顺-facial ö -bridged polarofacial与它们一起系统抗-facial异构体。
• Building BLOCK Strategies for the Synthesis of Molecular Clefts with Inside Functionality
  作者：Ronald N. Warrener、Davor Margetic、Ananda S. Amarasekara、Douglas N. Butler、Indu B. Mahadevan、Richard A. Russell

  DOI：10.1021/ol9905396

  日期：1999.7.1

  A new general route to U-type cavity structures (molecular clefts) with inside functionality has been developed using wall extension or base/ roof assembly methods which draw upon (i) the 1,3 dipolar cycloaddition reaction between alkenes and cyclobutene epoxides (ACE coupling) or (ii) the Diels-Alder reaction of alkenes with fused dihydropyridazines (s-tetrazine coupling). In this way, functional units (e.g., crown ethers, redox active naphthalenes) have been attached stereospecifically to short-walled bis-alkenes 1-5 to produce cavity structure 6-10 with top of-wall separations (C to C) from 4.5 to 12.7 Angstrom.