2,3-dihydro-2-hydroxy-3,3-dimethyl-1-indanone | 135366-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,3-dihydro-2-hydroxy-3,3-dimethyl-1-indanone
• 英文别名: 2-hydroxy-3,3-dimethyl-1-indanone；2-hydroxy-3,3-dimethyl-indan-1-one；2-Hydroxy-3,3-dimethyl-indan-1-on；2-Hydroxy-3,3-dimethyl-1-indanon；2-hydroxy-3,3-dimethyl-2H-inden-1-one
• CAS: 135366-62-0
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: ZYLHGPHDTFANBL-UHFFFAOYSA-N

物化性质

• 熔点：
  111-115 °C
• 沸点：
  309.4±41.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2-hydroxy-3,3-dimethyl-1-indanone 在 lead(IV) acetate 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以1.91 g的产率得到3-hydroxy-4,4-dimethylisobenzopyran-1-one
  参考文献：
  名称：

  摘要：

  Crystal and molecular structures for aryl- and benzyl-substituted 3-hydroxy-3,4-dihydroisobenzopyran- 1-one are described. For the 4,4-dimethyl derivative, two monoclinic modifications are produced on sublimation: (1) P2(1)/c, a = 23: 668(6) Angstrom; b = 11.749(4) Angstrom; c = 7.215( 2) Angstrom; beta = 96.70(2) degrees; V = 1992: 6(10) Angstrom(3); (2) P2(1)/c, a = 11.509(4) Angstrom, b =12.429( 4) Angstrom, c = 6.933(2) Angstrom, beta = 91.12(3) degrees, V = 991.6( 6) Angstrom. In both, hydroxy groups are pseudoaxial, and molecules form dimeric complementary but noncooperative hydrogen bonds. In the 6-methoxy derivative (3), P2(1)/c; a = 14.185(7) Angstrom; b = 4.105( 4) Angstrom; c = 15.598(13) Angstrom; beta = 98.59(6) degrees; V = 898.1(10) Angstrom(3), the hydroxy group is pseudoequatorial, and the intermolecular hydrogen bonding forms infinite chains. In the 4,4-dimethyl-7-nitro derivative (4), C2/c, a = 19.365(4), b = 8.425(2), c = 13.464(4), beta = 92.62(2), V = 2194.2(7) Angstrom(3), the hydroxy group is pseudoaxial, and the intermolecular hydrogen bonding forms chains. Compared to the unmethylated compounds, the interbond angles within the ring at the dimethylated carbon are contracted.

  DOI：

  10.1023/a:1024226029750
• 作为产物：
  描述：

  3,3-二甲基-1,2-茚满二酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 2,3-dihydro-2-hydroxy-3,3-dimethyl-1-indanone
  参考文献：
  名称：

  Photochemical Reaction of 3,3-Dimethyl-1,2-indanedione with Xanthene

  摘要：

  详细研究了3,3-二甲基-1,2-茚满二酮（DMID）与氧杂蒽的光化学反应。产物为1-羟基-3,3-二甲基-1-(9-氧杂蒽基)-2-茚满酮（3a）（49%）、2-羟基-3,3-二甲基-1-茚满酮（13%）、1,1′-二羟基-3,3,3′,3′-四甲基-1,1′-联茚满-2,2′-二酮（5a）（23%）和9,9′-双氧杂蒽（6）（49%）。反应通过DMID的3(nπ)*氢

  DOI：

  10.1246/bcsj.51.3047

文献信息

• Adam, Waldemar; Prechtl, Frank, Chemische Berichte, 1991, vol. 124, # 10, p. 2369 - 2372
  作者：Adam, Waldemar、Prechtl, Frank

  DOI：——

  日期：——
• THE REACTIONS AND ENOLIZATION OF CYCLIC DIKETONES. V. (1) SOME CARBONYL REACTIONS
  作者：C. F. KOELSCH、C. D. LeCLAIRE

  DOI：10.1021/jo01204a005

  日期：1941.7
• Photochemical Reaction of 3,3-Dimethyl-1,2-indanedione with Xanthene
  作者：Kazuhiro Maruyama、Atsuhiro Osuka、Yoshinori Naruta

  DOI：10.1246/bcsj.51.3047

  日期：1978.10

  The photochemical reaction of 3,3-dimethyl-1,2-indanedione (DMID) with xanthene was investigated in detail. The products are 1-hydroxy-3,3-dimethyl-1-(9-xanthenyl)-2-indanone (3a) (49%), 2-hydroxy-3,3-dimethyl-1-indanone (13%), 1,1′-dihydroxy-3,3,3′,3′-tetramethyl-1,1′-biindan-2,2′-dione (5a) (23%), and 9,9′-bixanthenyl (6) (49%). The reaction proceeds via hydrogen abstraction by 3(nπ)* of DMID leading to triplet radical pair composed of its semidione radical and 9-xanthenyl radical. The product 3a is a combination product from the radical pair, while 5a and 6 are escaping products from it. The hydrogen abstraction occurs at C-1 carbonyl group of DMID in a fairly efficient quantum yield (Φ=0.71). Behavior of the DMID semidione radical is rather resemble those of open-chain semidione radicals than those of sterically hindered semidione radicals.

  详细研究了3,3-二甲基-1,2-茚满二酮（DMID）与氧杂蒽的光化学反应。产物为1-羟基-3,3-二甲基-1-(9-氧杂蒽基)-2-茚满酮（3a）（49%）、2-羟基-3,3-二甲基-1-茚满酮（13%）、1,1′-二羟基-3,3,3′,3′-四甲基-1,1′-联茚满-2,2′-二酮（5a）（23%）和9,9′-双氧杂蒽（6）（49%）。反应通过DMID的3(nπ)*氢
• ——
  作者：W. John Cooper、Tyler N. Smith、Andrea K. Barker、Jason A. Webb、Edward J. Valente

  DOI：10.1023/a:1024226029750

  日期：——

  Crystal and molecular structures for aryl- and benzyl-substituted 3-hydroxy-3,4-dihydroisobenzopyran- 1-one are described. For the 4,4-dimethyl derivative, two monoclinic modifications are produced on sublimation: (1) P2(1)/c, a = 23: 668(6) Angstrom; b = 11.749(4) Angstrom; c = 7.215( 2) Angstrom; beta = 96.70(2) degrees; V = 1992: 6(10) Angstrom(3); (2) P2(1)/c, a = 11.509(4) Angstrom, b =12.429( 4) Angstrom, c = 6.933(2) Angstrom, beta = 91.12(3) degrees, V = 991.6( 6) Angstrom. In both, hydroxy groups are pseudoaxial, and molecules form dimeric complementary but noncooperative hydrogen bonds. In the 6-methoxy derivative (3), P2(1)/c; a = 14.185(7) Angstrom; b = 4.105( 4) Angstrom; c = 15.598(13) Angstrom; beta = 98.59(6) degrees; V = 898.1(10) Angstrom(3), the hydroxy group is pseudoequatorial, and the intermolecular hydrogen bonding forms infinite chains. In the 4,4-dimethyl-7-nitro derivative (4), C2/c, a = 19.365(4), b = 8.425(2), c = 13.464(4), beta = 92.62(2), V = 2194.2(7) Angstrom(3), the hydroxy group is pseudoaxial, and the intermolecular hydrogen bonding forms chains. Compared to the unmethylated compounds, the interbond angles within the ring at the dimethylated carbon are contracted.